The program is excellent about surrounding you with world class peers that make you move faster and work harder. It isn't really an educational program though; I think some folks think there is more training in YC than there really is - you spend your time focused on building your own startup. As for achievements, we were proud to raise our seed round at the beginning of YC.
First hire was a designer; 2nd & 3rd hires were engineers. All hired during YC.
Honestly the solo founder part is rough - I would not do that again
The biggest mistake was waiting too long to start to build out our marketing efforts; it takes a long time for that to build up
As for the long term vision of Courier, the goal is to provide the kind of abstraction to communication that exists in spaces like payments. You no longer have to worry the difference between accepting Mastercard vs VISA vs AmEx - developers should be able to easily send and receiving messages to/from their users across the channels best for that particular user in much the same way.
@james_conor Thanks for all the answers! A couple follow ups: why did you end up raising at the beginning of YC instead of at the end, say after the demo day? Would you recommend starting to fundraise before and during YC?
I had begun raising a friends & family round when I first went full-time, under the assumption I wasn't going to get into YC. I ended up getting connected to a partner at a VC firm (Matrix Partners) who was our ideal possible investor - he had led product at Twilio, the biggest player in our space, and deeply understood the problem we were solving.
I talked it over with the YC partners and their take was that I could probably get a slightly better valuation if I waited until demo day, but not a more applicable first investor. FWIW I definitely am glad I made the decision I did.
As for my recommendation: I recommend running your business in a way that doesn't rely on getting into YC, as that is outside of your control. Raise capital when your business would benefit from it.
@james_conor Hi Troy, it's great to hear that everything is going well for you. Just to jog your memory, we worked together in Washington DC. Could you share your experience of making your initial hire?
@muzzi Hey! I can't tell who you are from the username but PM me so I can say hi properly!
I'll skip our first hire (our designer), since that was someone I had worked with twice before.
Our second hire was our first engineer (besides myself, I suppose) and I found her on Angel List. That was tough. You're looking for the kind of person that can move really fast and is okay with ludicrous amounts of uncertainty. Finding that profile is no cakewalk, but convincing them to join is even harder. I think those early hires are probably comparably challenging as to pitching investors.
@james_conor What are some of the mistakes you think you could've avoided,in your entire journey,from starting to build your product to applying to YC?
@613jono There wasn't really time between starting and applying to YC to make any mistakes since I applied so early; all of the mistakes came later.
The biggest mistake across the entire journey was waiting too long to start to build out our marketing efforts; it takes a long time for that to build up.
@mishamarie While probably not a "surprise" but the biggest difference is of course how much time has to be spent thinking about other aspects of the business, in particular marketing & sales. I've found that to be challenging as someone that really just loves to constantly "build."
I think the biggest surprise, for me, is how much I love spending time with customers. I had some exposure to that in past roles (including as CTO) but only a small fraction of my time; most of my time was focused internally. I thought that'd be a big friction point for me but it turns out it is the highlight of my job.
I suspect that is more of a "founder" thing than CEO thing though. I started Courier because I had the pain that I was setting out to solve myself, so whenever I have a chance to talk to people about how we're solving their problems (or even in cases where the feedback isn't so positive) I get incredibly energized.
@sehnsucht9 Honestly I don't have a good answer for that. Being a solo found has been a struggle and continues to be one even years later. I'd strongly advocate for finding a co-founder, but I want to make sure folks understood that isn't a requirement for doing YC.
A couple follow ups: why did you end up raising at the beginning of YC instead of at the end, say after the demo day? Would you recommend starting to fundraise before and during YC?
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