My Y Combinator Experience with Lively (W17)
We knew getting into YC was a long shot, but we applied anyway. We were two non-technical co-founders, we hadn’t written a line of code, and we had no product-market fit. We were the perceived epitome of companies that shouldn’t apply to the world’s most renowned technology accelerator program.
If I’m being honest, I think YC saw something in us that we probably didn’t see in ourselves at that time. Nonetheless, they took the bet and away we went into the most intensive 10-week period of our lives. It was intense because we knew we had one shot at propelling the business forward and if we didn’t perform, we wouldn’t raise the necessary capital to grow the business. Having the luxury at looking back on things now, it is likely that the business would have failed had we not gone through YC.
The idea of YC was first introduced to us by our early investor, Point Judith Capital (PJC). They really pushed us to apply. We were hesitant at first. It’s never an easy decision to give away 7% of your company, but we ultimately decided to take the plunge. The way we thought about it was if we perform during our time at YC, we have to believe that the value of our company would increase by more than that — spoiler, it did.
I was living in Boston with my family at the time. My wife & I decided that if we are going to give ourselves the best chance at being successful with Lively, we had to be out West. So, we decided to put our house on the market and began looking for places to live in the Bay Area. As this was happening, Alex & I applied to YC (4 weeks late) and we ended up getting the interview. I remember it being a very hectic time. I flew out for the 10 minute in-person interview on December 14, 2016 and found out that we got into YC that evening. I then took a red eye back to Boston that night just in time to close on the sale of our house on December 15th. It was a surreal 24 hours.
My wife & I spent the next 3 weeks transitioning from our life in Boston — saying bye to friends, packing, and planning for our new life in the Bay. Our official one-way ticket was on January 12, 2017. YC started on January 3rd, so I ended up doing two more 24 hours trips before our official move!
We stayed with our friends for a couple of weeks before our things arrived and within the first 24 hours of our arrival, we had two separate urgent care visits — one for my wife and one for my 19 month son! Off to a good start. Nonetheless, we made it through and finally moved into our own place.
We had no idea what we were in for, but the YC experience was awesome. We had weekly dinners where YC brought in a bunch of cool speakers — Ron Conway (SV Angel), Mike Maples (Floodgate), Patrick Collison (Stripe), Brian Chesky (AirBnB), and many others. One thing always stayed with me from these dinners and that was something that Brian Chesky said. He said that they are building a company meant to last the next 100 years. I have tried to bring that same kind of thinking into Lively so that we don’t take too much of a short-term view that may jeopardize our relevance down the road.
We had no idea what we were in for, but the YC experience was awesome
Additionally, we had workshops, office hours, a network of founders who have encountered all sorts of things at our finger tips. The resources and the sheer amount of talented people around us was nothing short of amazing.
YC is an incredible forcing function to push you beyond what you think you are capable of doing. While most companies in our batch were reporting on weekly growth metrics as we got together, we were often left with a feeling of inadequacy. Early on, we felt as though we didn’t belong because we didn’t have much to offer —we didn’t have a functional offering. We were too busy getting our bank contract signed and building V1 of our platform, not growing like everyone else.
That feeling soon changed. One thing after another kept clicking. We got our bank contract signed, we had finished up all of the initial designs and work flows, our MasterCard debit card was ready to be produced, and our engineers were cranking away. We even hustled our way to get some early customers on board. We knew that we needed some chart that was going up and to the right for demo day!
On March 1, 2017 at 3:01am PT, we set our site live and Lively was open for business.
It was a very emotional moment for many reasons. It was a personal sense of accomplishment. Having moved my family over 3,000 miles for a dream, this had to work. Launching was great, but it was just the beginning. We were balancing getting new users, fixing bugs, talking to investors, finding more users, etc. We were an unknown entity, but we still managed to get people to trust us with their healthcare dollars. We never took that lightly (and never will).
I’ll talk about the lead up to Demo Day in a separate post, but it’s also worth noting that while YC was an unbelievable experience, it came with very difficult moments and personal sacrifice. I spent an unsustainable amount of time working during YC to ensure we were doing everything possible to make our time at YC worthwhile. The people who suffered were my wife and my son. My wife was left having to navigate a new geographical area while also starting a brand new job and dealing with my son. An ask that in hindsight was completely unfair. I sacrificed my sleep so the time that I did have with them wasn’t as energetic as I wanted it to be. Lastly, trying to build a start-up in the Bay Area with a family is difficult (not impossible). There are certain financial requirements that come along with a family. Don’t get me wrong — this wasn’t a surprise, but it wasn’t pleasant. Fortunately, we got through it all. I am so incredibly grateful to my wife for always believing in me and giving me the opportunity to pursue my dreams, even when at times it meant her sacrificing hers. I know this wouldn’t be possible if she wasn’t supportive.
People always ask “would you have gone through YC knowing what you know now?” My response: “In a heartbeat!” I could have been smarter about a couple of things, but such is life. You do the best you can with what you know at the time and hope for a better tomorrow.
