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We rode the hour and a half to Napa rehashing the interview (which itself wasn’t even 15 minutes long) with me thinking it went well and Chad thinking it went poorly. The interview certainly wasn’t what we expected, but I liked the vibe. I felt like they liked us. I thought that we would be a good fit with YCombinator and that they felt so too.

When John called we both gave him our thoughts on the interview, and he didn’t know whether to be encouraged or discouraged (though he knew my people reading skills to be far superior to Chad’s) but either way it didn’t really matter, the deal was done and there was nothing left to do but wait. They’d told us they were going to call that night and let us know either way. I admired their efficiency. The whole process, from the moment we saw the applications were starting back up to the time we’d know if we were accepted was about 3 weeks. Not much in the business world moves at that pace.

We stopped for lunch at Brix (though only because the line at Mustard’s, my favorite lunch spot so far in the Valley, was overcrowded) and checked in at the hotel, deciding to just surf the internet until the call came. Just as we were getting back from the hotel’s complimentary wine tasting (and judging by the quality, it was still overpriced even for free) the phone rang with an unfamiliar area code on the caller ID. I told Chad, who by that point had devoured every last fingernail out of nervousness and I think was getting ready to work on the toes, “well, this is it.” It was Paul Graham. “We’d like to invest in your company.” We were in.

He told us the deal they were offering and it was well within the range we had discussed, so I accepted on our behalf immediately. I’ve read articles and blog entries from a few different people who say that the YCombinator deals are unfair to founders. As they say in their FAQ, they usually give $5,000 + another $5,000 for each founder, so in our case we expected $20,000, for an amount between 2 and 10 percent of the company, with an average of 6. That alone is a valuation, even at 10%, of over $180,000 (and nearly $1 million at 2%) for what is essentially nothing but an idea from someone whom they’ve spent 10 minutes with.

Also, they have expenses that I have to think are non-trivial, so there’s more to it than just the dollar amount for the funding. This is a full time job for one of them, and I don’t know how much time the other three spend, but it seems significant. And they have connections and, most importantly, wisdom, and that you couldn’t buy for any amount. In just over 3 months I’ll be presenting what we’ve built to a virtual who’s who of the tech industry. The VCs who’ve funded most of the major tech companies will be there, and I’ll have a great shot, especially because I have multiple people who’ve done it before coaching me along the way. That opportunity alone is worth a few percent of any newly formed web startup.

And I think YC could ask for more of the companies and get it from almost all of them, so from a supply/demand standpoint they’re actually overpaying. I won’t say what they purchased from us, but we would have given them more. I get the feeling from meeting them and talking to previous YCombinator alumni that they want to help others succeed as much as they want to make money for themselves. As far as I can guess, they seem to be doing a great job of both, but either way I don’t think their deals are at all unreasonable. And judging by the number of applicants, neither do most prospective founders.

So after we found out we were accepted we called the families and then drank a celebratory bottle of champagne in the hotel bar. Sunday was spent wine tasting around Napa. I’d arranged a tour/tasting at Stags Leap Wine Cellar, where I’m a member, and Pete gave us taste of all of their fantastic wines. We did a late lunch/early dinner at the Rutherford Grille, which had an out of this world prime rib sandwich (thanks for the tip Pete) and did a light dinner at Bistro Jeanty, which had this fantastic tomato soup in a puff pastry.

Monday we took a trip back down to Mountain View to meet up with the YCombinator folks and some of the teams that were chosen. They gave us an overview of the program and it was pretty encouraging. The key for me will be presenting to the VCs in August. Being the least technologically experienced founder in my group but the most social and most accustomed to the non-tech parts of The Project, my main goal is to build up hype among potential customers. So while Chad and John are focused on getting the site operational as soon as humanly possible, I’ll be worrying about getting some people to use it before showing what we have to all of the major funding sources in the industry. Not much could give you a better incentive to make a kick-ass product than knowing you’re going to be talking to the guys behind every web startup from Amazon to Zillow, and our trip to the YCombinator office got me pretty excited to have such an opportunity.

We also spent a little time looking at Dexter. That was kind of neat and kind of scary at the same time. When the computer uprising comes, it’s going to be anybots doing the killing. I just hope to get on Dexter’s good list before that time comes. Maybe I’ll sneak him a flask of motor oil when nobody is looking.

After that we drove back to Napa and did dinner at Bouchon, on recommendation from PG and a couple others. It was fantastic, and leagues better than the one at The Venetian. Just like at Bistro Jeanty they were out of escargot though, prompting me to think there was some sort of nationwide snail shortage. We’d seen one large enough to make a steak out of on the way in, but unfortunately it was gone by the time we left so I went home snailless.

On Tuesday night we moved into the city, since our flight out the next morning was early. We cabbed down to North Beach to have a couple drinks with Lisa, a high school friend, at Rogue Brewery’s little bar by Washington Square. After that I had arranged a dinner with the team behind Xobni. A couple of the non-Justins from justin.tv came along too, as well as Pete and Ian, two British founders also accepted into this summer’s session, and a Canadian hacker girl named Laurence (hope I spelled that properly) who will soon be working for Trulia. We did dinner at a little Thai joint in the neighborhood. It was pretty good, but I’m spoiled by a place in my area called Suk Ho Thai. The name is rather unfortunate (either they didn’t have someone who speaks English green light it, or they did and that person hates them) but it’s still my favorite Thai restaurant.

After that we moved over to some little bar nearby with Pete and Ian (everyone else was abstaining since it was a work night) and had a couple drinks while discussing our projects and the impending move to Boston. Talking with the Xobni guys had made us realize just how much work this project is going to be, not just these next four months or so, but, if we do well, for at least a few years. Instead of saying to each other “dude, we’re going to Boston” or “dude, we got into YCombinator” as we did for the first couple days, we’re now saying “dude, I’ve got a lot of work to do.”

This weekend Vicki and I will be heading to Boston to look at a number of apartments I’ve lined up through Craigslist. After that it’s going to be a crazy month of wedding planning, getting the house ready, fixing the computers we’re going to be using for our development environment, and working on The Project, getting it set for its mid-August demo and hopefully a late July semi-public beta. Moving is going to be a tremendous pain, and we’re not sure yet whether we’re going to be taking furniture or just trying to rent it there. The latter may actually be cheaper, and is definitely far easier. I guess I’ll find that out pretty soon.

I hate flying. Since I’ve done it so much over the last couple years I’m not nearly as fearful of it anymore, but the anxiety has been replaced by annoyance. I’m starting to think my YCombinator submission should have been for a teleporter.

On the way to the airport traffic was at a complete standstill. I had left pretty early (definitely the first time I’ve ever given myself that much wiggle room) and barely got to the gate before boarding began. If not for my having learned to pack lighter and fly carry-on I never would have made it in time.

When I got the airport it turned out that our plane had had some serious maintenance problems and was replaced by a smaller craft, meaning 35 people were getting bumped. Luckily Chad had shelled out some change for a first class ticket and I am an Elite member, otherwise I suspect we both would have been bumped. We had to ride in coach (I already knew I wasn’t getting an upgrade) and Chad got a voucher for doing so.

So we got in, rented our car, and drove down to Mountain View. It was less than a half hour haul from the airport. I took a walk around just to see what the place looked like, and it was actually pretty nice. There were mostly smaller homes with very small yards (I’m not in Kansas anymore) but they were well-kept and well-manicured. It looks like the area I grew up in, only richer and whiter.

We stayed overnight at the Holiday Inn Express, which actually wasn’t a bad place. It even had a kitchen, and free Wi-Fi. Chad put the finishing touches on the demo while I tried to make up for lost sleep, since I knew I was going to be doing most of the talking and had been up for way too many consecutive hours. Thanks to a dose of Tylenol Nighttime large enough to tranquilize an elephant, I awoke well-rested and on a good sleep schedule.

I’m writing this now on the trip from Mountain View up to Napa (don’t worry, Chad’s driving). Our brief time at YCombinator was eye opening. First we talked to a couple of guys from Xobni, who have a pretty neat idea going. They were one of last summer’s founding groups I believe, and afterwards they came out to San Fran to live. One of the members actually made me think about how to lower the barrier to entry of The Project for people who aren’t familiar with that sort of thing. He said something to the effect of “make something 10x easier to use and 1,000x more people will use it” and I think that’s a great idea for us to keep in mind. Parts of The Project can be a little esoteric, so that in and of itself has probably made this entire trip worth it.

We got called in for our interview a few minutes behind schedule. It was very brief, and I really wish we would have had an hour to talk about all of our ideas. We barely got to scratch the surface of why we are so much different and better than our competition. We also didn’t even really get to show them the demo we’ve spent the last week and a half slaving away over, but I’m ok with that anyway, since not a second of that time was really wasted. It was all spent learning tools necessary to this and other potential projects, and if nothing else coming out here made us actually start laying down some code.

I personally thought the interview went very well. Jessica Livingston called out “Matt Maroon” and then told me she’d been waiting to call that one out all day. I guess she likes my name. Richard Brodie did once tell me it sounds like a rock star’s name, maybe there’s something to that.

The reception from the three (Jessica, Paul Graham, and, when he returned from the restroom, Trevor Blackwell) was rather warm. They asked us mostly questions about our idea. Why it was different from the competition, why we thought it would be successful, tons of other issues. They threw a few curveballs at us too, because our idea is basically taking another idea (which is basically an online implementation of a rather old brick and mortar activity that has had functionally no innovations in over 20 years) to the next level and they were sort of one more step ahead of us on that. That also gave us some food for thought, more for features to add down the line than for anything in the beginning I think, but still very helpful.

And Paul complimented me on my composure. He said that most of the founders were very nervous, voices wavering and all. Had I had more time I would have told him the best poker story of all, which comes from Shut Up and Deal by Jesse May. When the protagonist is asked what the difference between the small stakes games and the higher ones is, he says “the color of the chips.” Everyone thinks that’s a wiseass answer, but it’s not, it’s the truth, and it applies to every aspect of life. And once you internalize it, there’s no such thing as nervousness anymore.

So, on the whole, this has been a great experience whether we get accepted or not. It jumpstarted our project. It made us pump out a visual representation of our web interface, which definitely put us all on the same page. Whereas before we all had very different ideas in our head of what all it entailed, we now have a concrete representation.

At the same time, I think I want to be accepted more than ever into the program. From talking to the other founders, and even just the other prospective founders, I felt a strong sense of community, not just among the alums, but in the tech startup world as a whole. It’s very, very much like poker in that regards, the people involved all know each other. And even though everyone was there today competing for a spot in YC, of which I get the impression only about 1 in 4 groups will get, we all were rooting for each other. We left to another group saying they hoped we got to spend three months together in Boston, and we genuinely hoped so too. I met at least 10 people today, and all of them I hope to see again.

Also I found out that Paul Graham is somewhat of a gastronome too. Should make for some interesting conversations in Boston.

(*Note: all of the above was written on the car ride after the interview. Even though I wasn’t able to post before knowing the conclusion, which is soon to follow, I edited only for grammar*)

As a total internet addict/wannabe web startup founder I’ve been a pretty big Paul Graham fan for a while. He’s one of those guys whose words almost always ring true. I read them, and even though I have little experience with them, and can’t test them empirically because they are largely abstract theory, I just know they are logically correct. It’s the same feeling I used to get when reading the Theory of Poker back before I started playing. I’m a sucker for a well-crafted essay.

So a friend and I had been in the research stages of a project that I can’t really talk much about just yet (heretofore known as “The Project”) for a couple months. I went to Paul’s website to look up something related and lo and behold I noticed that YCombinator‘s summer funding session application deadline was a little more than a week away. I’ve been reading about that program since its inception and thought it might be worth a shot, so I talked to my cofounders (John and Chad) and we all agreed to fill out the application.

YCombinator is, as far as I know, the progenitor of a new type of funding. They invest in companies in the earliest stages, and do so in a rather unique way. They buy a small amount of the company for a small amount of money. The founders all have to move to their location (Boston for the summer session) for 3 months and spend the time working on their project. In our case the small amount of money they’d invest isn’t really too meaningful (I could pull more out of my wallet) but the advice, contacts, and weekly meetings with Graham and the other founder groups are invaluable. I’ve read a number of things from founders who’ve participated in past sessions, and it looks like a great opportunity.

So when we decided to apply we had, by that point, spent more hours than I can count fleshing out the idea, researching the various technologies available, forming a general business plan, looking into a possible patent application, and so on and so forth, so filling out the application was pretty easy. We felt good about our chances, even though we knew we were underdogs. Hundreds of groups apply for every session and relatively few are invited to meet with the YCombinator folks out there in Mountain View. Of them only a handful are accepted.

So we were pleasantly surprised on April 10^th when we received an email saying they’d like to hear more about our idea at their offices in Silicon Valley. We didn’t spend much time celebrating though, as we quickly realized that we wanted to get there with something to show them. We’ve spent the time since then coding and designing, day in and day out, trying to ready a demo. The Project is rather unique, so we felt that it would be much easier and more effective to show it to them rather than just try to describe it.

We’ve made considerably more progress over the last eight days than any of us really thought possible. In fact, we’ve learned so much in such a short time that we’re now convinced that if accepted, we’ll have at least most of a working prototype ready by the time we get to Boston in June, and probably a beta shortly thereafter. Certain aspects of The Project turned out to be far simpler than we had initially anticipated, and much of the design/code we’ve done for the demo will be useful in creating the beta version.

So Chad and I leave for San Francisco early on Friday. We’re staying overnight in Silicon Valley, doing our brief presentation/interview thingy Saturday morning, and then heading up to Napa for a few days of much needed rest and relaxation. That’s probably my favorite place on Earth (sorry Vegas, you’re a close second) and since I hate flying I figured that if I’m going to go through all of the expense and effort of getting to one Valley, I might as well visit the other. American Muslims probably don’t fly to Saudi Arabia without visiting Mecca, and gastronomes similarly don’t visit the bay area without stopping by St. Helena.

It sounds like we’ll know Sunday night whether or not we were accepted, so we’ll need some wine one way or the other. Champagne to celebrate, or a good Cab for consolation. I have a good feeling it will be Champagne though. We have a great idea, and we’ve made what I feel is an excellent demo of it. And, most importantly, we believe in ourselves. We believe in our ability to make this product and get a beta up and running. We believe in our ability to learn what it is customers want as we grow and then serve it to them as we mature. We believe in the ability this product to make a ridiculous sum of money.

In fact, our building this demo has cemented our resolve to push forward even if YCombinator decides we aren’t the right fit for them. We have the funding to get all the way to a beta version, and I feel we’d then have little trouble getting more. So we’re definitely optimistic about YCombinator, but most importantly we’re optimistic about The Project either way, and that’s a good spot to be in.