One of our ideas before going out to California to build Wufoo, was to document our journey live. It sounded like a good idea and I think a lot of the other Y Combinator startups were hoping to do that too, but in all of our blogs you’ll notice that it always trails off after the first week. That’s because blogging while creating creating a startup is like trying to write a diary entry on a rollercoaster (which is why I’m completely amazed by the Carsons’ fortitude while building Amigo ).

It’s been almost a year since we accepted seed funding from the investors of Y Combinator. Since accepting that first check, we’ve quit our jobs, moved to the other side of the country (and back) leaving behind two cubicles (gladly), a corner window office (a little reluctantly) and our girlfriends (lost one in the process and married another), established incredible friendships with some of the most talented developers and entrepreneurs of our generation, holed up in a room together for 4 months (powered by rice, ramen, hot dogs and Sunkist), lost a collective 45 pounds (gained back about 15) and built something that will probably be one of the defining moments of our lives. There were some hard times and there were some impossible times, but there are zero regrets about taking that check.

I think for a lot of startups and investment companies, the story stops at their product’s interface. Outside of some paragraphs in an infrequently updated blog (because they’re incredibly busy), you judge and measure the success of their ventures by the products alone. That’s a really small story.

And so in light of the recent fury of attention coming to Kiko, Paul Graham, the upcoming deadline for the next round of potential founders, and in an effort to document the experiences while they’re still somewhat fresh in our minds, I’m going to try and dedicate the next couple of weeks writing a multi-part retrospective of our experiences in the program and what it was like building and raising funds for a web application startup in Silicon Valley. If you can’t tell, we’re really big fans of the process. Y Combinator is just one of those programs that’s unlike anything I’ve ever seen. It offers people with real talent, real opportunities. This doesn’t mean everyone is guaranteed success, but you really feel like if there’s anyone that can help you make something big happen in your life, they can put you in the right place with the right people to earn it.

Now, I do think we have a fairly unique perspective, which is why I really want to write this, that might be of interest to a lot of people curious about going out on your own. We were bootstrapping another company for about 4 months when we applied to the Winter Founders Program. We were determined to build something regardless of whether we received funding. Our YC company was actually our second company and unlike a lot of the other founders in the program, we didn’t graduate from Ivy league colleges (two of us are actually MBA dropouts!) and we didn’t come from Fortune 500 companies. We just loved building stuff and hated working for other people.

I’ll try to get some of the other founders and even the investors of Y Combinator to chime in when I can to make this a little more interesting, but really I want anyone that’ll read it to get a better understanding of this relatively tiny and intimate world we were in and get a chance to know the people (my god, the people!) outside of the hype, generalizations and speculations you see all over the web. In fact, I remember what it was like for us applying to Y Combinator. It was a big giant mystery to everyone. I remember being intimidated and nervous and afraid because these guys were geniuses and millionaires.

And because I remember how nerve-racking that was, I want to try and reduce the anxiety for those of you on the fence about applying or following the investment route. I want you to send us all the questions you’re afraid to ask about taking investment from Y Combinator or other Angel investors in general because you’re worried about sounding ridiculous. If you’re thinking about applying but are worried about some issues or want to know about the application process and how to increase your chances of getting picked, ask us. Put them in the comments or send it to me at kevin[at]

I’ll try to answer as many as I can on Monday and answer others that I don’t get to in our retrospective over the next few weeks. Yes, we’re still in the middle of everything and its early for us, but we were able to make a lot of smart decisions because of the generosity of others. This is just a way for us to give back appropriately.

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Kevin Hale

Send Us Your Questions about Y Combinator by Kevin Hale

This entry was posted 4 years ago and was filed under Notebooks.
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  1. Someone · 4 years ago

    How much did Y Combinator contribute to you guys securing Angel funding? Could you guys have gotten it on your own?

  2. Kevin Hale · 4 years ago

    Hey everyone, I just realized that the whole required email might make this awkward. I’ve made it optional for the rest of this weekend.

  3. Mike · 4 years ago

    Why did you guys give up on bootstrapping?

  4. WebAdventure · 4 years ago

    I started working on a new web 2.0 service (on my own so far). I don’t need funding at this point; I have enough savings to last me for a while until I know weather my venture is worth continuing on. Do you still recommend getting funding? Will they provide valuable help other than the money? Or, should I continue on my own for a while longer and if it works out, I’ll end up with a higher share when I eventually take funding?

  5. David Stone · 4 years ago

    Hi Keven,

    Re: the Carsons’ fortitude while building Amigo

    .. I’ve got number of articles that I’m trying to find time to write for still… and when I was ‘coding on full steam’ through the dev I didn’t get much written for it compared with what I wanted to!

  6. Elza · 4 years ago

    You have a wonderful website here. May God rich bless you always.æ