Third Time’s the Charm: My Journey of Resilience, Failure, and Renewal at ISB

My road to ISB was anything but straight. It moved through safe jobs, unexpected turns, failed ventures and surprising resets. Each chapter taught me something new about myself, often the hard way.

What kept me moving was the stubborn belief that it is never too late to start again.

When I finally joined the PGP PRO Class of 2026, I felt ready to stitch those lessons into something meaningful, armed with resilience, humility and the hunger to grow.

Lessons From Failure: Falling and Standing Up

Leadership had first found me in school, when I was chosen as Headboy. At the time, it felt like a badge of honour. Over time, I realised it meant much more, it was about showing up for others and taking responsibility even when unprepared.

At VIT Vellore, where I studied Electronics and Communications Engineering, I joined the Robotics Club. What began as curiosity turned into a defining experience. First as Treasurer and later as President, I learned how to raise sponsorships, rally teams and make robotics education accessible to more students. Looking back, the real lesson was not in the events or funds raised, but in enabling others to succeed.

After graduation, my first job was at Standard Chartered Bank. It was secure and prestigious, but within months I knew I wanted something more purposeful. I left to become a Junior Research Fellow on a DRDO project at VIT. Managing a research team and collaborating with defence stakeholders taught me patience and rigour. Still, the urge to build something of my own kept tugging.

That urge turned into Trikon Technologies, a 3D printing startup I co-founded with college friends during the pandemic. We hustled hard, even secured early revenues, but funding was scarce and our runway too short. Shutting it down was painful. It taught me that grit mattered, but timing mattered even more.

My next step was Edmingle, an early-stage SaaS startup, where I grew from Key Account Manager to the Founder’s Office. This time, I learned leadership could also mean nurturing what already existed and helping it grow stronger. Around the same time, I adopted Archie, my golden retriever, who brought discipline, joy and balance into my days.

Archie even inspired my second startup, Zoomies, a pet-friendly cab service. We bought a second-hand Ertiga and drove the first rides ourselves. Customers loved it, but investors found the idea too niche. Without funding, we shut it down. 

Ironically, two years later Uber, Rapido and Namma Yatri all launched their own pet-friendly services. Each time Uber came up in Prof Shilpa Agarwal’s Managerial Economics class at ISB, I smiled at the bittersweet memory. Sometimes you can be right, just too early.

A Hospital Form: The Reset I Did Not Expect

By then, I had weathered two failed startups and was drained financially and emotionally. I was moving forward at Edmingle but lacked clarity on my next step.

The turning point came when I was admitted to a hospital with Dengue. Lying weak in bed, I stumbled upon the ISB PGP PRO application form. Almost casually, I filled it in, expecting little. To my surprise, I was shortlisted and eventually accepted.

That acceptance felt like a reset button I had not known I needed. It was the universe nudging me to start fresh.

From the first weekend, ISB was a whirlwind. Classes were demanding, professors inspiring and peers incredibly diverse. Every case discussion pushed me to challenge assumptions. Even casual coffee chats turned into mini masterclasses.

Balancing my role at Edmingle, weekend learning at ISB and Archie’s boundless energy at home was not easy. But every debate, assignment and reflection felt like a step closer to becoming a sharper and more thoughtful leader.

The Realisation: Why Third Time Was the Charm

At ISB, the scattered lessons from my past finally came together. Resilience, timing, structure and curiosity found shape in frameworks, case studies and peer learning. For the first time, I was not just reacting to situations, I was anticipating and analysing with clarity.

If I could give future applicants advice, it would be this. Do not wait for the perfect time, because it does not exist. Be prepared to be stretched, because that is where transformation happens. Come with humility, because learning flows as much from peers as from professors. And above all, trust the process, because it will prepare you in ways you cannot predict.

Two failed startups once felt like setbacks. Today, I see them as stepping stones. ISB gave me the mindset, structure and network I had lacked earlier. Whether I move into product leadership, step into a Chief of Staff role or launch another venture, maybe even a Zoomies 2.0, I know I will approach it with resilience and clarity.

Leadership is not about having all the answers. It is about being willing to learn, unlearn and start again. And for me, the third time truly was the charm.

Synopsis

Debopam Dey, PGP PRO Class of 2026, reflects on his unconventional path to ISB. From student leadership to failed startups, from hospital recovery to classroom rigour, his journey shows how resilience and humility can turn setbacks into stepping stones toward purposeful leadership.