How to Apply to YC: The YC Application Broken Down & Translated

I was fortunate to be part of Y Combinator’s 2014 summer batch. With each following application cycle, I have been asked by friends and friends of friends to help with their application. I found myself saying the same thing in different ways so I thought I would do my best to try and provide some tips and ‘translate’ the application. I will explain the thought process behind each question and then provide an example answer.

I will use Thumbtack as a case study. They are not a YC company but I am big fan of marketplaces (and Thumbtack!). Also, hiring a professional for a service is a problem with which many of us are familiar. Please do not take any statements below as fact. Thumbtack is just my example.

I will also skip a few questions that do not need explaining (e.g., category, corporation, etc.)

I hope this helps.

Question: Describe your company in 50 characters or less.


Do not use “X for Y.” Before you freakout and say that YC has always recommended this method, let me put you at ease with two of Sam’s most recent tweets.

"Very few of the best startups I have been involved with could describe themselves as "the X for Y". 

"Also, this is an example of something I've changed my mind on--I used to think startups should strive to describe themselves this way."

X for Y triggers too many different responses. It contains two vectors with innumerable connotations and is a poor way to get your point across.

“Uber for Y.” Uber means different things to different people: a logistics network, a food delivery service, a courier service, a cab company. It could also imply that I will use something four times a day.

Keep it simple! “Press a button and a car comes to you in minutes.” That was 49 characters with the period and very few people will come away from that with radically different ideas. They may differ on its ultimate potential or possibilities but they will understand what your product does from day one. You need to survive day one to get to day two. To use PG’s example, there is no need to explain “your Microsoft” here, only your Basic Interpreter.

Example Answer:

Marketplace to hire professional service provider.

Character Count: 50 with the period :)

Question: What is your company going to make?


Keep this answer simple and direct. You will not be accepted based solely on this answer but you might get thrown into a separate pile if you cannot clearly explain what your company is building. The act of communicating what you are building in a straightforward (i.e. simple and concise) way is one of the most underrated skills. This will come in handy in all aspects of running your business, from raising money to convincing potential employees to join your team to acquiring customers.

Example Answer:

We built a marketplace to find the best provider for home services in your area (e.g., plumber, painter, exterminator, etc.).
Thumbtack focuses exclusively on the introduction between the customer and the experienced professional. Finding the right contractor is the key pain point when hiring a contractor for your home. It is not, for example, paying them.
We solve this problem with our unique bidding system. A customer fills out a project-specific form and receives a project-specific quote from experienced professionals. We require professionals to pay for each bid they submit and show the customer the first 5.

Question: Please tell us about an interesting project, preferably outside of class or work, that two or more of you created together. Include urls if possible.


This does not have to be software related. This question is meant to learn more about you as an individual.


Does this team have experience working on something together? What are your hobbies? How do you choose to spend your time? Chris Dixon once said, “What the smartest people do on the weekend is what everyone else will do during the week in ten years.”

Example Answer:

We both lived far from college and flying home was super expensive. Some of our friends from other countries used localized airline sites (because they were in their native language) and we noticed they had cheaper flights! So we built a web app that saved us thousands of dollars on flights over the course of a few years by doing two things.
  1. Checking each airlines localized sites and throwing our IP address to that location. Airlines change their prices based on the location of the potential customer.
  1. Using our intended destination as a “connecting” airport. For example, sometimes flights that connect through Chicago are cheaper than direct flights to Chicago. You simply don’t fly on the second or third leg.
It was a fun hack that eventually got shut down. We learned how to work together and that showering is very important when working in close quarters.

Question: How long have the founders known one another and how did you meet? Have any of the founders not met in person?


Be honest and personal! Getting to know someone via a questionnaire is difficult if you don’t meet YC halfway.

Example Answer:

We met sophomore year of college (6 years ago) in a Masterpieces of Western Philosophy class, a mandatory class at Columbia University. We started arguing about the existence of free will in the latter part of the class and our discussion continued to lunch. We’ve been best friends ever since and, in fact, the argument continues to this day.

Question: How far along are you?


Pretty self-explanatory. Include both raw numbers and percentages. Fight the urge to puff things up even a bit.

Example Answer:

We are currently in a private beta in San Francisco.

We launched 5 months ago and here are our key metrics:
  • 650 completed projects (50% MoM growth)
  • 150 Contractors Signed Up, 3200 potential customers
  • 1900 bids (close-rate ~34% lifetime but increasing as network grows)

Question: What is your monthly growth rate?


This is your opportunity to show that you understand your KPI and have a sense of which metrics matter most to your business. PG wrote, “Merely measuring something has an uncanny tendency to improve it.” Show YC you know what to measure.

Example Answer:

  • Potential Customers: 45% MoM
  • Contractors: 35% Mom
  • Completed Projects: 50% Mom
  • Close-rate: 9% MoM
We think the close-rate is the most important metric right now. It represents the liquidity of our marketplace. It is increasing as we grow, which is a sign that we are seeing strong network effects.

Question: Why did you pick this idea to work on? Do you have domain expertise in this area? How do you know people need what you’re making?


This question, and the next question, are the two questions on which you should spend the most time.


  1. Why are you passionate about this idea? How do we know you won’t give up at the first sign of trouble? Are you willing to spend the next decade on this idea?
  2. Why are you uniquely suited to solve this problem?
  3. Have you validated this idea? Have you tested it out?

Example Answer:

1/2. I picked this idea to work on for two reasons.
First, My dad was a contractor for 43 years and I have experienced the problem of getting new clients first hand. Getting new jobs was hard. From the ages of 7–18, I was head of business development for his company☺, which meant hanging flyers on every single lamp post in town every Saturday for 11 years and responding to every single Craigslist request for a contractor. Each time he would have to give references and justify that he and his team could do the job. AND the majority of the customers didn’t know the right questions to ask to help us give a quote. Often times, they ended up just going with their friend’s plumber even though my dad was obviously better!

Second, finding a contractor is an absolute nightmare. For example, how do you trust a person contacting you on Craigslist, or the flyer on the street? Can you verify their references?

What questions do you ask them to receive an accurate quote?

When your toilet doesn’t work is it because it is: clogged? not flushing? flushing slowly? constantly flushing? fills slowly? overflowing? leaking pipes? unpleasant oder? wobbly handle? How is the building connected to water and sewage systems? Municipal? Well water? Septic? You get the point. It sucks.

3. People need what we are making. Every single person with a roof over their head needs what we are making. When a stranger enters your home, you need to make sure it is the right person. The introduction is everything and that is where we excel! (growth explained in other questions)

Question: What’s new about what you’re making? What substitutes do people resort to because it doesn’t exist yet (or they don’t know about it)?


This is the time to explain your unique insight. What have you figured out that no one else has? And, most importantly, what is it replacing? This is one of the most important questions on the application.

The first question is there to assess the novelty of your idea. What is the value that your company will add?

The second question is there to assess the marginal benefit of your idea. Is it 10x better than alternatives? It must be 10x better. Note that a substitute does not have to a company or product. It could simply be a time consuming or inefficient process.

For example, Snapchat enabled people to send disappearing pictures (the new). People had to either resort to trusting the recipient entirely (even if simply an ugly selfie) or not send the picture (the substitute). Evidently, neither option was sufficient.

Example Answer:

Currently, people looking to hire an experienced professional are powerless. We change that. By creating a system in which multiple experienced professionals bid for a job, we provide a transparent and efficient market for home services.

Before we existed (or for those who haven’t heard of us yet), people had to resort to archaic means of finding a professional. They could either search through Craigslist and hope for the best or call friends and use who they had used — with a limited sense of what the market has to offer.

We also provide an incredible customer acquisition channel for our contractors. It isn’t just that customers have trouble finding great contractors but contractors have trouble acquiring new customers. We help grow their business.

Thumbtack is quite the matchmaker.

Question: Who are your competitors, and who might become competitors? Who do you fear most?


Do not shy away from your competitors. This question is not meant for you to say, “We have no competitors. We have found an untapped billion dollar market.” This is an opportunity for you to show that you understand the competitive landscape and how you differentiate. Show you have immersed yourself in the industry and know it better than anyone else — that is what will help you crush them!

A competitor isn’t always someone doing the exact same thing. A competitor is simply an alternative from the consumer’s perspective. While Facebook competed with other Social Networks, Airbnb competed with the hotel industry and Amazon competed with Borders. Understanding the alternatives, and why your solution is 10x better, is crucial to acquiring customers.

In this question, show you know your stuff. Again, do not shy away from your competitors but rather analyze the heck out of them and be honest with your fears…it is the only way to overcome them!

Example Answer:

We have a lot of competitors: Amazon, Google, Angie’s List, Handy, RedBeacon, HomeAdvisor.

We fear Amazon and RedBeacon.

We fear Amazon because it has almost unlimited resources. They do not need to profit from this arm of their business. We do.

We fear RedBeacon because they are focusing on the exact same market but with a different model. They take a commission from the contractor when they ‘win’ a job.

Most importantly, no one is mainstream. The winner has yet to be determined in this fragmented and inefficient market. Ultimately, assuming each player executes, the winner will be the model that scales in the most cost-effective way. We believe the winning model is one that charges for a bid (similar to an advertisement) and not one that takes a percentage of the sale. Contractors understand paying for a lead, they have trouble with the idea of a broker or an agent.

Question: What do you understand about your business that other companies in it just don’t get?


This question builds on “What is new about what you’re making?” In that question, you explain the what. In this question, explain the why.

For example, Snapchat’s what is disappearing pictures but the why might be fear of judgement (immediate and 10 years later). Evan Speigal puts it very succinctly when he says, "I’m the result of everything I’ve ever done, but I’m not really the accumulation of all that stuff."

The why is why your product resonates with users. Explain this here.

Example Answer:

It is all about the introduction! There has been a recent trend in marketplaces to handle the entire transaction life cycle. From introducing the two parties, to handling the communication during the interaction, to facilitating payment. For some marketplaces (e.g., Uber & Airbnb), this makes sense. Enabling payments to occur seamlessly solves a pain point in the interaction and adds significant value.

However, in our case, this is not the main pain point and not where we can add the most value. When people hire a painter, the pain point they experience is not paying them $3,000 after they have completed the job.

People have been paying painters without too much trouble for years. BUT, finding that painter is an utter nightmare and that is where we come in. By focusing exclusively on introducing the contractor and the customer, all of our energy is spent solving the largest problem, while others are focused on the entire life-cycle.

Question: How do or will you make money? How much could you make?


This question, more than any other, is not about giving the ‘right’ answer but about showing how you think. Show you know your market, make reasonable assumptions, and extrapolate from there. Do NOT calculate your potential revenue with a Top-Down approach. Saying you only need to get 1/10 of a percent of a trillion dollar market is ridiculous. It ignores the process. The process of getting the first customer, then the second, then the third and so on. This is what YC wants to see. 

Use the Bottom-Up approach (example below).

Example Answer:

We make money by charging contractors to bid for potential customers. It replaces a portion of their advertising budget. Rather than hanging a flyer on a lamppost, posting on Craigslist, or taking an ad out on Yelp, they know they have AT MINIMUM a 1/5 chance of acquiring the customer. When the job is between $250 and $3000, spending between $5–25 to get the job is money well spent.

Our ultimate goal is to replace our contractor’s entire advertising budget. We want to be how they acquire new customers. Currently, our contractors spend ~$2000/month on advertisements (~10% of gross revenue). They spend money on door hangers, refrigerator magnets, post cards, yellowpages, and more recently FB and Google ads (of which most contractors have only a minimal grasp).

Approximately 1/1000 people in the United States is a plumber (note, Thumbtack is far more than plumbers). If we assume that a major metropolitan area (e.g., San Francisco) has a stronger concentration of plumbers (1/300), then we can estimate there are 2800 plumbers in San Francisco.

Currently, our contractors are providing ~10 quotes/month with an average of $10/quote (5% of their advertising budget). If we assume this rate is maintained, $100/month ($1200/year) for 30% of plumbers in San Francisco, that results in just over $1MM per year. This is exclusively from plumbers solely in San Francisco. Nevertheless, we believe this rate will increase as our close-rate increases, the network expands, and we are able to drive more business their way.

This number increases significantly when we include:
  • Other experienced professionals (painters, exterminators, electricians)
  • Additional cities (San Francisco only has ~850k people)
  • A larger slice in contractors advertising budget (we can do better than 5%)
We don’t know how large the market is but it is safe to say that the size ultimate size of the market is massive. It will not be an impediment to the success of Thumbtack.

Question: How will you get users? If your idea is the type that faces a chicken-and-egg problem in the sense that it won’t be attractive to users till it has a lot of users (e.g. a marketplace, a dating site, an ad network), how will you overcome that?


This is the time to show how methodical you are about your business. Be specific. Emphasize the repeatable ways in which you have acquired users. 2500 users from ProductHunt, while awesome and a strong validation that people want what you’re building, is not as strong as acquiring 2500 users from a scalable source. YC wants to see that you have experimented, that you drilled, and after turning over every rock, have found a well.

Are you scraping Craigslist/Yelp and emailing/texting potential customers? How many do you email each day? What is the response rate? If your main source of new users is from advertisements, what channel? Why? What is the click through rate? How much are you paying per download/click? How does that compare to the estimated LTV of each customer (i.e., do the unit economics make sense?)? Or are your users coming from events, partnerships, blog, youtube, social media, or cold-call sales? Regardless, be specific and break it down.
This is an opportunity to open the kimono and show YC how your brain works. The best YC interview is ultimately a conversation where you open your brain to them and have a dialogue about your business. Think of the application as an extension of that dialogue.

Example Answer:

Thumbtack is a two-sided network, which means we face the chicken and egg problem. The challenge is to grow both sides of the marketplace at the right pace so that both sides are satisfied.

Supply Side: We solved the initial supply-side problem by building a strong single-player utility for contractors.

We knew that contractors’ primary source of new clients was Craigslist but it was incredibly difficult for them to manage. We built a tool that streamlined posting/re-posting and responding to potential inquiries. Each post included a “powered by Thumbtack” at the bottom.
As a result, contractors were able to receive value from Thumbtack from day one, even without the “demand” side of the marketplace. They “came for the utility” and have ultimately “stayed for the network.”

We found these contractors by scraping thousands of databases across the web to find the exact location of these professionals. We then created extremely targeted advertisements to get them to sign up.

123/150 (82%) of our contractors have used this tool prior to responding to a customer inquiry. Of the 123 that have used the tool 86 (70%) have submitted a quote within 3 weeks.

Demand Side: We have 3 main channels through which we acquire potential customers.
  1. Craigslist posts (35%): they were extremely well formatted and redirected back to Thumbtack, which attracted many potential customers when they searched on Craigslist.
  2. Direct Search (47%): We have manually created over 1000 unique forms for potential jobs (e.g. painter, plumber, air-condition repair). As a result, we appear extremely high in search results for most home-related services.
  3. WOM (18%): Thumbtack is awesome and people tell their friends :)

Question: Please tell us something surprising or amusing that one of you has discovered.


Keep it short and simple. To quote Aaron Harris, “If you’re not sure whether a joke will land…don’t tell it.”

Example Answer:

The way people play pick-up basketball is the way they approach life.

Question: What convinced you to apply to Y Combinator?


Don’t write an answer that you think YC wants to hear. And don’t make this a tough question for you. Be honest. YC is probably the best bullshit detector I have ever come across.

Example Answer:

That’s a tough one. There are many obvious reasons: the network, funding, advice etc. But for me, it is a bit more simple than that. A few of my friends have participated and each one has said it was an inflection point in their life. I want that experience.
I trust them.
Thanks to Cleo Abram, Henri Stern, Ryan Shea, and Amy Buechler for reading drafts of this.

How to get free AMC/Regal Movies (Orig: June 9th, 2015)

For those of you who don’t know me, I see a lot of movies. I love going to the theater, getting a large popcorn/diet coke, and watching a movie. I will see anything! My in-theater record is 8 in one day. This can get expensive. Tickets in NYC can exceed $20. So, as a kid, I developed a few cost saving mechanisms (not all of which I am proud).

To name a few:

  • Purchase tickets at the AAA website to receive bulk discounts
  • Fold up the popcorn bag and bring it back for the next movie (rip it first and apologize so you receive a new…less disgusting bag)
  • Pay for one and see multiple (classic)

But then a few weeks ago, I found out how to get FREE MOVIES!

Even as a kid, I loved loopholes. Much to the chagrin of family and friends, I would exert more effort reading the rules/terms of service than actually playing any game or thinking about a promotion.

It had the feeling of a chess match: you versus the company.

The company has devised a system that, by design, will be profitable (whether because of the program directly or because of the accompanying positive externalities). They believe they have created an inducement that will prey on consumer irrationality and the idiosyncrasies in human nature that make behavior economists giddy. So it’s fun to see if you can beat them.

Here is how to beat AMC:

Step 1: Become an AMC Stubs Reward Member

Rules of the Stubs Card:

  • $1/Month to be a member (current promotion => $8/year)
  • For every $100 you spend, you receive $10 in return
  • Every concession is automatically upgraded to the larger size
  • No online ‘convenience fee’ ($1.50/ticket)

Step 2: Purchase 14 tickets for a movie a few days in advance

Step 3: Use your newly earned $20 of rewards on the movie you actually want

Step 4: Return the original 14 tickets

This is the list of things actions where Stubs Points are NOT applied

The reason this works is because there is a disconnect between when the rewards are applied and the movie is scheduled to run.

All you have to do is purchase tickets a few days in advance, use the rewards you earned on those tickets to buy a ticket for an earlier movie, then return the original tickets.

If they synced the rewards to movie showtimes, this loophole would not exist. However, this would compromise the customer experience. Most movie theaters make their money from concessions (hence your $15 popcorn and soda). If customers had to wait to redeem their reward they would not be able to head straight to the concessions (no instant gratification) and pay ridiculous prices for a few cents worth of corn and carbonated water. They would have to wait until the next time they visited the movies to use the rewards.

NOTE TOS: AMC can terminate at any time for any reason

I have only done this once to see if my theory worked. Basically, I am no longer a kid testing my limits or a student to see as many movies as possible but I still enjoy finding the holes in a system. My youthful, movie-going indiscretions left me guilt scarred so I actually contacted AMC to let them know about the issue. My sharing this is only to point out a cool loophole.

Would love for others to share loopholes they have found in the comments.

Why Airbnb brought my family to tears (the good kind) (Orig: May 29th, 2015)

My father had his first heart attack and a stroke at the age of 39. In an instant, the fulfillment of his life’s purpose ended. He could never return to his practice, his research was to be completed by others, and he retired from medicine. For the last 20 years, he has been a full-time dad.

Unfortunately, what I know of him as a physician was gleaned from the discretely disguised stories related in the medical jargon physicians use at neighborhood barbecues and holiday celebrations.

That was the case until two weeks ago when I finally convinced my sister to list her apartment on Airbnb for the summer. Within a few days she had an awesome tenant with whom she enjoyed a few pleasant exchanges. Then she received an email from the tenant’s mom that brought my sister to tears. I have included it below (Names & places redacted).

Dear Bri,
My name is [], and my daughter, [], a junior at New York University, will be your new tenant this summer. When my dear friend, [], found your apartment on Air B & B, he sent me your name along with the address of the apt. Upon reading your name, I was flooded with emotion.
In 1987, I was a 27 yr old professional singer and songwriter in NYC: a blonde waif living with a longtime boyfriend, and your father’s healthy patient. That yr began happily, but by summer, while pregnant with a child I wanted, I became nearly paralyzingly exhausted and a lymph node protruded from my neck… Another doctor of mine ran blood tests and said I had the Epstein Barr virus and to absolutely not have a biopsy… But additionally, I went to your father who, in the sweetest yet firmest tone, told me I WOULD be having a biopsy, immediately. And he would be guiding me no matter the results… Within weeks I was diagnosed with a stage 3B lymphoma, a very advanced stage, and then your dad, along with his partner, Dr. [], walked me through the bleakest time of my life: I would have to end the pregnancy to save my own life, and begin an arduous journey of surgeries, and chemotherapy…. It was a year of hell, and this was a long time ago in the world of chemo…
I do not say this lightly or mellow dramatically: Your father and Dr. [] were like angels in my life. They treated me like gold. They sometimes did the thinking for me when I was too sick or bereft to think in my own best interest. They never made me sit for long in the waiting room… They held my hand. They found me the best oncologist in NYC, listened to all my questions and made me laugh and hugged me. I can say with sincerity, not only did they save my life, they did it like angels. I remember when you were born. And your dad had these huge, beautiful pictures of you and your brother adorning all the walls of his office…
I was told that -given the chemo at that time- I would probably never be able to conceive because all my eggs would be killed…. It was heartbreaking news. But miraculously I DID conceive and have a daughter and a son. And my beautiful girl will be living in your apartment this summer!
8 million people in the city, and our lives intersect in this way… It made me cry.
When your dad left his practice in the city it was sad for me… But and husband and I moved and raised our kids in Montana… I sure hope your parents are well and I send them my love. They knew me as []…
Love to you,

Airbnb’s economic impact is obvious and has few limitations. This summer, they approach one million rooms rented each night but what will not be chronicled in the cold rationality of a milestone reached or in the countless articles written about Airbnb’s success (and what can probably never be measured) is the exhilarating, mysterious alchemy of the human experience, which they enhance. They connect people through space and time.

Our legacies are not the aggregate of what we have accomplished but rather they are the ripple effects of each and every interaction.

It is how my father has lived each day and I have been a witness to the small gifts so many have received from the seeming small kindnesses. Still, I am grateful for the small glimpse into the physician my father was that was given me by my sister’s Airbnb tenant’s mom.

Thanks pops and thanks Airbnb.

Our Journey To and Through YC (Orig: Oct 10th, 2014)

Henri and I applied to Y Combinator an embarrassing number of times, four to be precise. A recent study of successful entrepreneurs revealed that certain qualities defined them, one of which was the ability to manage rejection and failure. We hope that is the case because we have had our fair share of practice.

We have learned most through our failures, both about our business and ourselves; so, as YC is accepting new applications, I thought I would share our experience.

March 2013

Applied and rejected from YC.

April 2013

In our senior year of college, we met Sam Altman. Remarkably, Sam was the sole person on PG’s list of top 5 founders whom we did not know. He spoke wicked fast and we did our best to reciprocate (not a good idea).

Like every college student at the time, we pitched a photo-sharing application. It was fun but it wasn’t something that kept us up at night. It sounds cheesy but it’s true: you have to work on the thing that consumes you. It never stops and it is as awesome as it is scary. With the photo app, we just weren’t there.

As we were leaving, Sam asked if we considered working on something else. I answered, “No. This is us.”

Later, I thought of Dr. Venkman in Ghostbusters when they were zapped by a demon after replying “No” to the question of whether the Ghostbusters were gods. He said, “If someone ask you if you are a god, you say yes!” Maybe I could have said yes but in the long run it is more important to be honest than “correct.”

If a YC partner asks you anything, just shoot from the hip. Bullshitting won’t help you and they have a sixth sense for what is real. Trying to finesse them only means you don’t believe in yourself or your product.

After sending a follow up thank you email, Sam replied:


Hey —

You guys were awesome. If you believe in the idea, you should definitely go for it.

Are you guys willing to consider other ideas, or are you really set on this one?


That was an excruciatingly polite way of saying your idea may not be all you think it is. I am glad Sam asked again. Henri and I did a gut check. Liking your idea is different than being consumed by it.

Finally, we re-submitted an application with a concept strongly reminiscent of Shout. That meeting with Sam was the catalyst that led us to create the entity we consider an extension of ourselves. We were invited to interview, flew out to California the next day, and prepared our pitch on the plane.

It was the first of our three trips to 320 Pioneer Way. There are things you always remember. Flying to California was a lot better than flying home after a rejection.

In a mere 12 hours, a roomy, light-filled miracle of flight transformed into a drab, metallic torpedo that had absolutely no business being suspended in air.

First Interview:

We were interviewed by Jessica, PG, Trevor Blackwell, and Robert Morris. The conversation was a blur. They didn’t fully understand what we were pitching and, looking back on it, neither did we.

It would be easy to justify why we might not be accepted: no users, no revenue, and no product. We didn’t even have a demo.

Still, I checked my emails obsessively (“Please, no rejection email”) hoping that my phone would ring instead. It never did. PG’s rejection read as follows:


I’m sorry to say we decided not to fund you. You seemed like energetic guys, but the idea is still so vague at this stage that it’s hard for us even to judge. Plus there is a lot of the “made up idea” about it. It seemed to us that if this happens it will be largely a delivery service that can get into buildings, which means it’s limited to campuses and even there not huge.



To that point, everything had been a bit too easy although, at the time, we didn’t realize it. We met Sam and a few days later we were pitching a fresh idea with nothing behind it. Nothing. Other applicants had moved their families, quit cozy jobs, and made sacrifices we only understand now.

In retrospect, I am glad we were rejected because they were right. We weren’t ready.

Learnings Part 1:

On the plane ride home, we made three decisions.

1. We would forgo our post-college plans (consulting & CS masters)

We needed to be committed, not simply impassioned. If we were going to bring people on the journey with us, we had to do it without a net.

2. I would learn to code

YC asked, “Which of you are hackers?” I did not have the skill that mattered most. That had to change.

3. Come hell or high water we were going to get into YC

Our egos were bruised but that is not why we were so motivated. The partners were intrigued by people trying to do something challenging and by the power of determined individuals to convert mere neuronal activity into a tangible reality. We wanted to be a part of that but, more importantly, we wanted to be worthy of it.

September — November 2013

I learned to code and Henri taught himself iOS.

The ultimate goal of Shout is to solve peer-to-peer local commerce.

We were fascinated by marketplaces and networks, but we needed to learn. So, we hacked together an app that enabled people to buy and to sell their spot in a line. It was the ideal experiment to discover what strangers needed in order to trust one another and to engage in a real-time transaction.

We worked non-stop and built the first version in 2 months. Then, two-days before the YC application was due, we locked ourselves in Henri’s brother’s apartment and wrote our YC app (Don’t do this!).

We stayed up waiting for the email to see whether we would get an interview. We must have read that first line a hundred times.


Your application looks promising and we’d like to meet you in person. Please go here to read how interviews work and sign up for a slot:

[ Link ]

If you haven’t already read this

[ Link ]

we encourage you to, because it answers most of the questions applicants have had in the past…

See you in California!


Second Interview:

This time felt different. We had a demo and over 1k+ on our wait list.

We were interviewed by Geoff Ralston, Michael Seibel, Garry Tan, and Sam.

Everyone understood what we were building. There was little doubt it was a potentially powerful tool. The main question, which was asked by Garry, was, “Do you think this is a good beachhead?”

We soon discovered they did not think it was.


I’m sorry to say we decided not to fund you. We think you are both very talented and that you should continue to pursue this space and find a great opportunity. At this point what gives us pause is that we are not sure that you have found a scalable and defendable usecase. We all think with another 4–6 months of development you will learn a bunch and might be in a much better position to re-apply. We look forward to seeing you again.




This time, I thought they were wrong.

We headed back to the airport and had dinner outside our gate. It was a Friday night and we were eating quesadillas in an airport bar before heading back to NYC after being rejected from YC…again.

That was a shitty meal. We ended up having the same meal 6 months later, at the same table, and let me tell you, that quesadilla was freaking delicious.

Learnings Part 2:

We may love Shout too much

It was at that dinner that we questioned whether we were going about things the right way.

Oddly, in a moment of extreme doubt, I experienced absolute confidence. We questioned almost everything about our approach except our working together. This is the sine qua non.

November 2013 — March 2014

Before Henri and I became partners, we made one promise: whatever happened, we would not fail because we did not work hard enough.

We launched our beta, finally resolved to achieving success sans YC. Wes (our Michelangelo on the team) joined us on the journey. All we needed was users. Perhaps we were a bit naive but, sometimes, not knowing you shouldn’t be able to do something is a gift.

We hired part-time actors (they are articulate, good-looking, and have flexible schedules). Then we went outside restaurants that do not take reservations and put our names down at around 5:30 p.m. When 8:00 p.m. rolled around and people were told there was a 2 hour wait, we offered our table to them — if they requested the spot on the app. We had it down to a science.

We didn’t stop there.

People started asking for deliveries. I became a Postmate to learn about deliveries. In February, there were a few Shouters who wanted tickets to SNL. We slept on the street in 4 degree weather outside Rockefeller Center several times; we are still searching for feeling in our toes.

Nothing else mattered, including YC.

Application time came around and we thought about not applying. It seems a bit silly to say now (to us), but it is true.

Unlike previous applications, we completed it with a cavalier flair.

Third & Fourth Interview:

For this interview, we prepared less. We had lived our business for 8 months. We had users and data.

Our first interview was with Paul Buchheit, Jessica Livingston, Trevor Blackwell, and Dalton Caldwell.

It went well but we could have done better. As we walked out, Tara told us that we weren’t done and had another interview.

We took a long walk between interviews.

We thought about how rare it was in life to get a second chance immediately after the first. We went into that final interview guns blazing because we weren’t taking that plane home with any semblance of regret.

Now, I thought of ‘Red’ in Shawshank Redemption. After years of caring about being paroled, and being rejected, he no longer saw his freedom as dependent on others; only then was he released. So it was with our team. We were ready in the only way that mattered, and it was palpable.

Learnings Part 3:

If you love something, don’t give up.

YC could sense it. YC takes companies when they can help a company most, not when they can make it. That’s the difference. The third time we interviewed we knew, and so did they, that regardless of the outcome we were going to be just fine.

YC can help you run faster but they won’t give you legs.

Y Combinator

Prior to entering YC, we received endless advice.

Surprisingly, it was mostly negative. Many drew the analogy to YC as an institution that would take out a hose filled with trite advice and simply spray each startup. There is no shortage of YC critics and, prior to experiencing it, I thought it possible that the criticism was justified.

I was wrong.

There are a few moments in my life that I see as inflection points. I understand the profound cumulative effect that can result from the confluence of all the seemingly benign events that led me to Mountain View— a la the butterfly effect — but you know what I am talking about.

YC was an inflection point.

“How could 85 companies receive a truly unique experience?”

Our YC experience was initiated with group office hours. I walked out feeling a bit dense but invigorated. My group’s office hour partners were Jessica Livingston, Paul Buchheit, Trevor Blackwell, and Dalton Caldwell. In our small group, we listened as the partners engaged with visual projection, microbiome, smoothie, nuclear, mobile app, and bitcoin companies—all in 90 minutes.

The conversation alternated between advice that was applicable to each startup and incredibly specific bits that were relevant to a single company.

Then they would turn on a dime into digging into the finer details of fresh food transportation and logistics, human microbiome sequencing, and visual projection device manufacturing.

It was incredible.

My partner and I left psyched. The partners were obviously terrificbut hearing the responses of the other companies let us know we were somewhere truly special.

It reminded me of my first night at Columbia. My new friends and I sat on the hall in our dorm and talked. As we shared our first night exchanging childhood stories, incredibly diverse stories of privilege and privation, I knew I was in the right place. There were no impenetrable barriers and no absolute requisites for inclusion other than a drive to learn. We were where we needed to be.

Later that night, we had our first Tuesday night dinner, the highlight of the week as well as an incessant reminder to get shit done.

Batchmates arrive early to spend time getting to know one another, share progress, and offer help.

YC is competitive in the best of ways. Everyone at YC wants to be the best. It is in their nature. That is exactly how it should be.

Yet, there is a sense of pay-it-forward in the YC community that I have yet to experience anywhere else…including my University. It is the most unique and powerful attribute of YC.

People can say it is an MBA in 10 weeks, helps you avoid common mistakes, and provides the forcing mechanism your company needs to reach its potential, which is true; yet, it is meaningless in comparison to what YC has given me. The quantifiable benefits of inclusion are not why they receive 7% equity.

This is best understood by looking at Sam’s new class at Stanford. At the conclusion of the course, his students might have notebooks identical to those cherished by each YC batchmate. Sam asks nothing in return but their attention and effort.

Why not?

Because YC is more than a “how to” course on running a startup.

YC is being able to knock on Jessica’s door at home and ask how to deal with a delicate conflict with an early employee.

YC is PB emailing you at 2 a.m. with strategy and roll out plans.

YC is Aaron Harris emailing us after every single newsletter with the right mix of advice and encouragement…weeks after YC has ended.

YC is Paul Graham remembering Henri and me after a single ten minute meeting 16 months prior, and commenting on the fact that we now had beards.

YC is Dalton running after you following the dry-run of your presentation to show you where the arc fell short, slide by slide.

YC is Alexis meeting your users at a coffee shop to check out what is means to be a Shouter.

YC is Kirsty saving you endless headaches so you can do what you do best.

YC is The Levy’s explaining the intricacies of YC Safes, Trademarks, and immigration law late on a Saturday night.

YC is Kevin skyping with you while you’re in a coffee shop in NYC, pointing the camera at the whiteboard, and going over the pros and cons of 4 different variations of post a page.

YC is sharing an elegant solution to a difficult and wide spread problem.

YC is using another company’s product before it’s better than their competitor’s, knowing what it will become is far more than what it is.

YC is a hike or bonfires with batchmates.

YC is a batchmate sending out a Tuesday dinner invite every week since YC has concluded.

It is an army, a cult, a family.

Month Post Demo Day:

The concluding speakers at the final YC dinner were the partners. They told us two very important things.

  1. Don’t stop. Don’t stop doing whatever you were doing that made you successful while you were here.
  2. YC is not over. It never is.

We aren’t sure where things will go from here. Shout may or may not succeed. But I know Henri and I feel fortunate to be a part of YC.

Thanks for reading.

Another Try (Orig: May 29th, 2015)

I have attempted to start a blog once before while in college. I told myself I would write one post a week. Unfortunately, it began to feel more like another homework assignment than a creative outlet through which I could collect and share my thoughts.

Writing is a process that I have loved always. However, since leaving school, I have found myself engaged in the process of putting my education to use instead of simply adding to it; consequently, I have not been able to dedicate the time (or mental energy) I once could, but it is something I miss dearly.

This time, I will not establish rules. I will write to share what is on my mind, give a few updates to friends and family, and hopefully return to a practice that brings me joy.

Hope you enjoy it.