Getting Interviewed twice in a YC Batch (S24)
My journey toward applying to Y Combinator (YC) didn’t start with a grand vision of building a venture-backed startup. It actually started with freelancing. Freelancing gave me the first taste of building something of my own—solving problems, delivering value, and getting paid for it. There was something exhilarating about owning a project, setting my rates, and being directly responsible for success or failure.
That realization planted a seed: I could take ownership of problems and create solutions that had tangible impact. Eventually, I started thinking beyond individual projects—what if I built something scalable? That’s when the idea of starting my own company became more than just a passing thought.
The Birth of an Idea: Construction Industry Pain Points
I’ve always known that the construction industry was incredibly fragmented. Through customer discovery, I found a compelling problem space: the inefficiencies in the bidding and change request processes. The bidding process is how general contracting firms win new business, requiring detailed cost estimations and precise documentation. Mistakes, inconsistencies, and inefficiencies in this process often lead to financial losses and operational setbacks.
We believed that AI could streamline and improve this process, offering contractors a smarter, faster way to bid on projects. With that goal in mind, I teamed up with two incredibly smart friends, Dominic and Prathik, to start building a prototype. Prathik, always the go-getter, even secured our first beta user by striking up a conversation with a general contractor on a live construction site. We quickly built a demo and began outreach efforts to validate our idea.
Applying to YC: First Startup, First Interview
Although we were still early in our journey, we decided to apply to YC. This was a first for me—I wasn’t deeply familiar with YC until Prathik explained its significance. We submitted our application, detailing our problem, solution, and progress.
To our surprise, we got an interview invite.
The first interview was nerve-wracking. YC interviews are notoriously fast-paced—10 minutes to convince some of the sharpest investors in the world that your startup has the potential to be a billion-dollar company. Our interview focused heavily on technical questions, our AI approach, and the market size. The partners wanted to understand how big this opportunity was and why we were the right team to tackle it.
Two days later, we received an unexpected email—YC wanted a second interview.
The Second Interview: A Rare Occurrence
As far as I know, being invited to a second interview within the same batch isn’t common. It meant YC saw potential but had unresolved questions. In hindsight, this was due to our failure to clearly articulate the problem and the exact value we could provide. The second interview dove into our pricing model, customer acquisition strategy, and go-to-market approach. We hadn’t adequately prepared for these aspects, and it showed.
Ultimately, we got rejected.
Reflections: Why We Didn’t Get In
The biggest lesson I took from this experience was the importance of storytelling. YC’s interviewers are incredibly sharp, but they still need to be convinced—quickly and clearly. We had an interesting problem and a potentially valuable solution, but we didn’t explain it well enough. If you can’t hook someone’s attention within the first 2-3 minutes, you’ve already lost them.
I also realized that strong technical skills alone aren’t enough. You need a deep understanding of your market, a clear business strategy, and an ability to communicate your vision succinctly. Our lack of preparation in these areas likely contributed to our rejection.
The Bigger Takeaway: From Freelancer to Founder
Despite the rejection, this experience solidified my belief that I wanted to build something of my own. Freelancing had taught me that solving problems and providing value were tangible skills I could own and design. The YC process reinforced that lesson on a larger scale—beyond just earning money, I wanted to create something impactful and lasting.
The rejection wasn’t the end. It was a stepping stone.
Advice for Others Applying to YC
- Clearly articulate your problem and solution. If an intelligent outsider doesn’t understand what you do in 30 seconds, you need to refine your pitch.
- Be prepared to answer tough business questions. Know your market size, pricing strategy, and customer acquisition model inside and out.
- Tell a compelling story. Investors aren’t just evaluating your idea; they’re evaluating your ability to communicate it effectively.
- Show traction, even if it’s early. Customers, users, and beta testers matter more than just an idea.
- Be concise. YC interviews are only 10 minutes long. Every second counts.
What’s Next?
This experience wasn’t a failure—it was a masterclass in pitching, business strategy, and startup storytelling. While that particular idea didn’t make it into YC, the lessons I learned will undoubtedly shape my future endeavors. I left the process with a better understanding of what it takes to build and pitch a startup, and I know this won’t be my last attempt.
YC or not, the journey of building and creating is just beginning.