Being an entrepreneur looks glamorous from the outside — news headlines focus on massive valuations and flashy exits. Sitting across from Harish Chandramowli, I was reminded that the day‑to‑day reality feels very different. Harish is an engineer turned founder who has worked in high‑security environments at Bloomberg and MongoDB and now builds AI‑driven startups such as Zeroshop.ai and Flare. When he says that entrepreneurship is a personal journey, he means it: “The version of me two years ago is wildly different from today”. In our conversation we dug into how he navigates growth, self‑doubt and emerging technologies — and why staying true to your values matters more than any buzzword.
What you’ll learn
- Resilience matters more than glamour. Behind every fundraising announcement are late nights, moments of doubt and high‑stakes decisions. Harish shared candid stories about working through uncertainty and recalibrating his mindset as his company grew.
- Solve a real problem first. His path from engineering to entrepreneurship started with noticing a painful gap in the market. The best AI products don’t chase hype; they address specific workflow bottlenecks for a narrow group of users.
- Trust in AI is earned. We talked about ethics and transparency — data must be collected and used responsibly if you expect customers to trust your systems. Harish believes consistent delivery and clear communication are what build that trust.
- Your origin story evolves. Harish encouraged founders to revisit their “why.” As he put it, the qualities that drove him when he started are not the same qualities he relies on today. Growth requires reflection and adaptation.
From engineer to entrepreneur
Harish didn’t set out to become a founder. He started his career as a cybersecurity engineer in the financial industry, working at Bloomberg and later at MongoDB. Those roles taught him to respect data, build robust systems and think about user security at scale. A few years ago he was in a New York boutique when he noticed a disconnect between what store owners needed and the tools available to them. Inventory, communication and operations were fragmented. That chance observation led him to co‑found Flare, a platform that helps fashion brands manage back‑office chaos.
Harish’s story illustrates a lesson many founders overlook: innovation begins with empathy. By listening to the frustrations of store managers and workers, he designed a solution that solved a real, felt problem rather than building features for the sake of novelty. That same mentality drives his AI work today. Whether he’s streamlining supply chains or automating security audits, he starts by asking, “Who is this for, and how will it make their life easier?”
Growing through uncertainty
Our conversation also delved into mindset. Harish admitted there were times he questioned whether he had what it took to run a company. He combats self‑doubt by surrounding himself with mentors and peers who challenge his assumptions and by revisiting his origin story. “The most important skill I’ve developed as an entrepreneur is the ability to stay curious,” he said during the workbook session. Curiosity keeps him learning from customers, data and even his own mistakes.
We discussed how he balances speed and rigor in fast‑moving sectors like AI. Rapid iteration is necessary, but so is ensuring that algorithms are fair and transparent. Harish emphasised that trust in AI comes from consistently delivering on promises and communicating how data is used. That means building feedback loops with users and being willing to slow down if a release could compromise ethical standards.
The long view on startup growth
Many founders chase growth at all costs, but Harish advocates for what he calls “scaling with soul.” It’s not about hockey‑stick metrics; it’s about creating a company that can endure. He recommends simple experiments to validate product‑market fit — targeted outreach, concierge onboarding with a handful of customers, or a value‑based pricing test. These low‑cost pilots, he argues, teach you more than any slide deck and help prevent over‑engineering.
He also touched on the importance of ethics in AI. When we asked him to fill in the prompt “Trust in AI is earned by consistently and transparently ,” his answer was “delivering results and communicating your intent.” In practice, that means making sure your AI doesn’t become a black box. He believes startups that respect privacy, explain their decisions and prioritize user consent will outlast those that treat customers like data points.
Final reflections
Talking with Harish Chandramowli left me both inspired and grounded. His journey reminds us that innovation is as much about listening as it is about coding. The entrepreneurs who succeed in AI will be those who combine technical excellence with humility and a deep respect for the people they serve. If you’re wrestling with your own startup’s direction or wondering how to incorporate AI responsibly, this episode offers valuable perspectives. Watch the full interview at the top of this article and take notes — your future self might be wildly different, too.