Startup Growth, AI, and the Entrepreneurship Journey – With Harish Chandramowli

The entrepreneurship journey is rarely as glamorous as headlines suggest.

Behind every story of soaring valuations and flashy acquisitions lies a tougher reality. Founders wrestle with self-doubt, face long nights of uncertainty, and make decisions that can alter the fate of their companies. In emerging industries like artificial intelligence and cyber security, these challenges intensify. The pace is relentless, risks are high, and the need to stay close to customers is greater than ever.

In this episode of The Best Business Podcast, host Daryl Urbanski speaks with Harish Chandramowli, a technologist turned entrepreneur. Harish has led engineering and security teams at global firms like Bloomberg and MongoDB. He now builds ventures such as Zeroshop.ai and Flaire. His journey began in a small town in southern India. It eventually led him to the heart of New York’s Times Square, offering lessons on resilience, innovation, and creating solutions that customers genuinely value.

The entrepreneurship journey demands persistence and the courage to solve hard problems. It also calls for a deep understanding of customers and the wisdom to adapt quickly in uncertain times. Tune in to hear practical insights and inspiring lessons that will guide you on your own entrepreneurial path.

Here are three reasons why you should listen to the full episode: 

1. Learn from Harish’s journey, starting in a small Indian town and leading to tech entrepreneurship journey in Times Square.
2. Discover why solving tough problems, listening to customers, and adapting fast are keys to startup success.
3. Explore how AI, privacy, and competition are reshaping business strategy in today’s evolving landscape.

Resources 

• Harish Chandramowli: LinkedIn 
• Zeroshop.AI: Website 
• Flaire: Website | LinkedIn
• Best Business Podcast with Daryl Urbanski - Where you can find more insightful interviews like this one.

Episode Highlights 

From Tamil Nadu to Times Square: A Global Entrepreneurship Journey

• The entrepreneurship journey is often portrayed as glamorous, but the reality is filled with self-doubt, long nights, and tough decisions.
• In fast-changing fields like AI and cybersecurity, the risks are higher and the need to adapt quickly is even greater.
• In this episode, Daryl Urbanski speaks with Harish Chandramowli, a technologist and founder who has navigated these very challenges.

Finding Momentum at Johns Hopkins

• At Johns Hopkins, Harish was surrounded by future professors, researchers, and entrepreneurs, which broadened his view of what careers could look like.
• Watching peers launch crypto startups while still in school showed him the value of autonomy, exploration, and learning by doing.
• The environment gave him exposure to non-traditional paths and sparked his own entrepreneurial ideas.
• While Johns Hopkins didn’t teach the entrepreneurship journey directly, it gave Harish the peers and perspectives that pushed him toward it.

Early Startup Lessons: From DIY Projects to Real-World Validation

• Harish and his roommates built RideEngine, a rideshare website in India created to solve a personal problem.
• Without ads or a marketing budget, the project gained traction and even media coverage. This is an early sign of strong product-market fit.
• Despite its promise, loans and responsibilities prevented them from pursuing it full time, teaching him lessons in timing and opportunity cost.
• This experience set a pattern for his career: solving real problems for real people through technology, marking another step in his entrepreneurship journey.

Why Fast, Customer-Centric Product Iteration Wins

• At MongoDB, Harish saw firsthand how staying close to the end user shaped success.
• Teams that combined speed with customer empathy consistently outperformed others.
• Daryl reinforces the wisdom: “The game is happy customers at a profit.”
• Together, they show why solving the hardest customer problems builds loyalty and allows premium pricing.

Learning to Sell Without Being “Salesy”

• Harish admits that sales was not natural to him as an engineer-turned-founder.
• His breakthrough came when he stopped leading with demos and instead focused on listening.
• By mapping out what prospects shared into flowcharts, he helped them see their own businesses differently.

Balancing Empathy and Execution in AI Product Development

• Trust is fragile when building AI products, so Harish’s team releases updates during low-use periods to reduce risk.
• When issues arise, they fix them immediately, even if it means manual corrections to keep customers running.
• Leading with honesty about what is new or still unpolished has been key to earning long-term trust.
• Daryl notes that while software enables massive scale, startups must work even harder to stay relevant in competitive markets.

Facing the Giants: Can Startups Survive AI’s Monopolies?

• A major question looms: what happens if giants like ChatGPT or Anthropic add your tool as a built-in feature?
• Harish acknowledges the risk but believes adaptability is the key to survival.
• Daryl points out that even big budgets can’t guarantee defensibility, as code alone is no longer a moat.
• Both agree the winners will focus on customers, offering hyper-personalized solutions while using AI as a multiplier.

Why the Entrepreneurship Journey Is the Ultimate Personal Growth Experience

• Harish reflects that he has grown more in two years as a founder than in a decade of professional work.
• Managing investors, hiring teams, and balancing constant demands has pushed him to grow on many levels.
• Founders must lead in uncertainty, guided by both data and intuition.
• For Harish, each stage of the entrepreneurship journey brings new challenges and insights, reinforcing the idea that growth never stops.

Final Messages on What It Takes to Build for the Future

• Focus on solving urgent problems that people will gladly pay to have solved. This is known as the “bleeding neck” principle.
• Don’t aim for a trillion-dollar company on day one; meaningful ventures often start small.
• Keep listening, keep iterating, and measure success by the number of lives improved.
• As Harish says, “Change is scary, but it’s a good thing. It has to happen for us to evolve.”