Dan and I had an unusual time applying to Y Combinator.
In September 2012 we started talking about the company that would become Standard Treasury. Primarily we were interested in why there wasn't an API platform that focused on ACH. It's a core payment type and is pretty much a pain in everyone's behind. Things came to head at Thanksgiving time, when Dan and I had dinner at a restaurant in New York City and hashed out a vision we had for a "Twilio for financial services".
After that, though, I interviewed and got an offer from Stripe in the first week of December. Then began a little bit of a dance. John and Patrick Collison were very generous with me while I tried to decide whether to work at Stripe or start my company with Dan. Many long emails were exchanged and the Collisons showed a huge amount of patience as I decided what to do. In the midst of that — in early December, two months after the deadline — Dan and I applied to Y Combinator for the Winter 2013 batch.
But, we didn't hear anything back from YC.
Dan was still working on Giftly and I was really in love with the Stripe team and culture. After a couple amazing phone calls with Patrick, I decided that I should go work at Stripe, really get a feel for startup life, and learn all I could.
I moved to San Francisco and the Friday before I was to start at Stripe we got the following email from Harj:
"thanks for the yc app. do you think you'd be able to make it to PA on Monday [my first day at Stripe] for a late interview? it's the day before YC officially starts but we'd like to meet you in person."
I had literally spent days making this big decision to go work at Stripe, not do my own thing, move to San Francisco (which Stripe paid for) all to have YC want to interview me at the 11th hour! Shit.
We didn't take the interview. It just didn't feel quite right.
But that one little email from YC likely made it destined that I couldn't stay at Stripe for long: that it likely wasn't going to work out for me there. That tiny bit of validation — which really isn't much validation at all when you think about it, they interview a lot of people — propelled Dan and me think about the idea more, to talk about the idea more, and to mention it to friends. Eventually I was bringing it up at Stripe and had a conversation with the General Counsel about how to handle my IP questions. Dan and I would be emailing people at Wells Fargo from our personal computers at night trying to figure out what was possible for our business, while I would be talking to other people at Wells Fargo during the day. We couldn't talk to venture capitalists, but we were socializing the idea with people, some of whom were even investors in Stripe.
That wasn't sustainable.
Stripe taught me a huge number of lessons about engineering culture, transparency, emailing writing, business development, and more. First and foremost though it partially demystified the startup world for me. I had worked in government before and held startups in awe. They are awe-inspiring. Building a company is so implausibly difficult. But in many ways when you're employee 37 at a startup, particularly one that is killing it, you think a lot about starting your own company. It only highlights the idea of being a founder. It only dares you to build a similarly great company.
So we applied to YC again. We got an interview, again. Again, I wavered and wasn’t sure that I wanted to leave a rocket ship. Again, we turned down the interview.
Then it all came together at the same time.
Dan’s company, Giftly, was sold — he knew the deal was coming together. That happened on a Friday. On Monday, Patrick and I had a serious talk where it was decided that I’d likely be happier if I did my own thing. In fact, my one-foot-in, one-foot-out approach hadn’t done Stripe any favors or made me particularly popular within the company, and it turned out to be better for both me and them that I move on.
On Monday night we emailed YC to ask for that interview we were offered. We emailed alums we knew. Several of them told us to “just go down there and wait.” Thankfully we didn’t have to make that decision. On Tuesday morning Kirsty, YC's CFO, emailed us. If we could make it down to Mountain View in an hour then we could interview that morning.
We were very nervous and frantic. We rushed down, driving 85 on the 101. Dan and I are practicing our pitch back and forth. We’re coming up with questions to answer. We are incredibly nervous. We hit traffic — you always hit traffic on the 101 — and we freaked out. We weren’t really prepared at all.
We arrive at YC, check in, and although we’re a minute late, so are they. We sit down to wait. When you’re waiting to interview at YC they have some alumni there to chat with you. To calm you down. They told us we would have a minute or two to present our pitch and then we would get questions. Try to be succinct. You’ll do fine.
We walk in and we shake hands with the partners. We begin to sit down and before our butts even hit the chairs, Sam Altman shoots “Isn’t your business just Dwolla?”. The rest of the ten minutes went by as a blur. 
That night I got the phone call. We had gotten in to YC. They made us the offer and I accepted. The phone call finished with Geoff asking, “Can you make our introduction session tomorrow morning?” Another trip to be taken on the 101.
 We either weren't aware of or very impressed by some of the existing solutions.
 One of Stripe's secret weapons is their General Counsel. He's a lawyer whose first instinct is "we'll find a way" not to say "no". [
3] During the drive from San Francisco to Mountain View, Dwolla had announced their Series-C led by Andreessen Horowitz