The Bobby Story: What We Built and What We Learned

We set out to solve a problem we experienced firsthand: the early-career hiring process is broken. Students send hundreds of applications into the void. Startups waste time sifting through mismatched resumes. And 70-80% of jobs are filled through referrals—leaving talented students without networks invisible to great opportunities.

Bobby was our answer: an AI-native platform that flipped the script. Instead of students chasing jobs, companies would come to them. Through natural voice conversations, Bobby would understand not just what students had done, but how they actually work—their values, their style, their authentic fit. Then we'd proactively match them with startups that aligned with who they really are.

We imagined Bobby as the career friend every student wishes they had - someone who actually fights for you, knows how to get you hired, and makes the whole process feel less like begging and more like being discovered.

Before Bobby: Hubble

We initially launched Hubble, a fully functional platform focused on student-startup hiring and gamified behavioral assessment. We ran a private beta and achieved early traction that validated our thesis: 300+ students signed up, and we onboarded two early-stage startups to test the recruiter side of the marketplace.

But validation alone doesn't make a sustainable business. We faced a combination of strategic and practical challenges: we delayed fundraising longer than ideal while infrastructure costs accumulated, both co-founders had full-time summer internships that limited our execution capacity, and user feedback revealed that incremental improvements wouldn't be enough - we needed a meaningful pivot.

Meet Bobby

After our internships, we applied to and were accepted into the IU Innovates Incubator with a new concept: Bobby. This wasn't a completely new idea - it was an evolution of Hubble, informed by everything we'd learned. We maintained our focus on student-startup hiring but shifted our approach toward voice-based agents, more intuitive workflows, and more refined matching algorithms.

We applied our lessons more deliberately this time. We participated in pitch competitions (and won some!), secured funding to support development, and relaunched with a working platform. We focused on validating assumptions through real users on both sides of the marketplace. The technology worked, the voice-agent was well integrated, and matching algorithm produced promising results. We felt like we had finally built something special.

The Hard Decision

I continued developing and iterating. I kept testing, refining, and talking to users.

But over time, a difficult truth became clear: Bobby wasn't delivering sufficient differentiated value to students. The core challenge wasn't technical execution - the technology was there. The challenge was that the marketplace dynamics and value proposition weren't compelling enough to drive the kind of organic growth and retention that would make Bobby sustainable.

Rather than continue without strong conviction, we made the decision to discontinue the project. At the end of the day, we learned what didn't work, and that's valuable too. I put some highlights (things like competitions, our founder cards in the incubator, etc.) photos below, feel free to take a look :)

Bobby may not have become the platform we envisioned, but the journey taught us invaluable lessons about building, launching, iterating, and knowing when to move on. We learned valuable lessons about shipping working software, acquiring users, and taking difficult decisions - both technically and strategically.

The skills, insights, and resilience we developed building Bobby and Hubble will inform everything we do next. Sometimes the most valuable outcome of a project isn't the product itself, but who you become in the process of building it.

The one thing I'm certain is that this was not my last startup or journey in entrepeneurship. I'm already looking for new things to build and problems to solve, and can't wait to apply what I've learned moving forward.