This story is part of our March 2026 issue. To read the print version, click here.

We asked former Startup of the Month founders to name one moment they remember from building your company that they didn’t recognize as pivotal until much later. Here’s how they answered.

Shweta Gandhi

founder and CEO of Strived.io, an AI-powered edtech platform that analyzes student data for actionable insights

It was the moment I ran out of money and paid my team on my personal credit card.

At the time, it didn’t feel like a big dramatic founder moment. It felt quiet, stressful and very real. I was thinking less about runway or strategy and more about the people who had trusted me enough to show up every day. That was the point where this stopped feeling like a scrappy experiment and started feeling like something I was fully responsible for.

That week became a true sink-or-swim moment. I couldn’t keep nudging the same plan forward and hoping it would click. I had to get honest about what wasn’t working, let go of some assumptions, and commit to a new strategy with real focus. Looking back, that moment forced clarity, sharpened my decision-making and fundamentally changed how I lead. I didn’t recognize it as pivotal then, but it shaped everything that came after.

Lisa M. Watts

founder and CEO of CREE8, cloud-based production and collaboration platform for creative teams

A moment I didn’t recognize as pivotal at the time was the first week we watched new users move from “trial curiosity” to real production behavior without needing us in the loop. It was not a big launch or a press hit. It was quieter. A team spun up cloud workstations, pulled media into shared storage, started editing while files were still growing, and coordinated across time zones like it was normal. No IT tickets, no “how do I set this up” calls, no heroics. They just stayed in CREE8 and kept moving.

Weeks later, that pattern became the clearest signal of product market fit: Speed and flow beat feature checklists. It also reshaped how we build. We started prioritizing time to value, predictable costs and fewer context switches over adding more knobs. That was the moment I realized we were not just shipping infrastructure. We were shipping momentum.

Ishita Shah

co-founder and CEO of Matrubials, a UC Davis spinoff developing therapeutics inspired by milk bioactives

Matrubials as a startup has focused on building therapies that women really need via products to reduce the burden of infections and subsequent secondary complications, including reproductive issues. Our technology can be leveraged simultaneously for additional infectious diseases, and we have deliberated on the regulated routes for the obvious reasons of clinical trial validation that can result in prescription by physicians.

We recognized a bit later that additional discoveries at our end can be channeled into a parallel path to bring to market a cosmetic, all-gender skin health product that can become our first revenue generating application as we continue to build the medical products. This vision brought about a pivotal shift in our portfolio expansion and marked the potential for diversification with the anticipation of impact far beyond our initial mission.

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