My Head Sherpa Fellowship Experience

As a founder going nearly broke, I started working part-time for an interesting organisation called Capria VentureBasecamp. I was hired as an Entrepreneur in Residence, and I quickly found myself getting involved in an experiment that evolved into the Head Sherpa Startup Fellowship. In this article I write about my experience as the MVP for the Fellowship 🙂

How it was born: Necessity (and accident) is the mother of invention

A month into my EIR stint, we faced an interesting problem: one of our incubator partners was delaying the deployment of our entrepreneur training program because they were struggling to recruit someone to run the program. As a stop-gap, I offered to take this responsibility upon myself until they found someone. Long story short: they never did, and I ended up delivering the entire program myself.

This accident was a highly valuable experience for the team, because not only did we get first-hand feedback about elements of our program, but we also realised an important constraint: even though we had a great training program, it was only as effective as the person delivering it to our audience. This brought our attention to the serious lack of good talent at most startup incubators in emerging markets. Later, based on my experiences, we fleshed it out into a fellowship for entrepreneurs to give back to the ecosystem by working with early stage founders, and get support/learnings for their own ventures. Thus, the Head Sherpa Startup Fellowship was born!

Getting started: Winning trust

It was a bumpy start, to be honest. I, an amateur first-time entrepreneur, was suddenly in a room full of equally (some even more) experienced founders, whom I was to lead towards investment readiness over the next 6 months. As founders, I’m sure they had developed a thick skin towards such programs, because they’re constantly being bombarded with Gyan. Hence it was difficult to get them to take me seriously. I overcame this by consistently showing up and offering to help in whatever way I could. It took 3-4 weeks for me to start building trust and being accepted into their lives. But once that bridge was built, we got along just fine and shared a wonderful rapport throughout the program.

A day in the life of a Head Sherpa Fellow

The Head Sherpa’s aim is to help their cohort startups achieve investment-readiness. This involves conducting workshops around the 12 Critical Success Elements, engaging with founders in 1:1 sessions to brainstorm on their specific problems, making connections with potential customers, hires, mentors and investors. Basically, anything and everything that would improve the odds of these startups getting funded. I started feeling responsible for the outcomes of these amazing founders, and found myself increasingly invested in their success over time. The program culminated with successful graduates of the program pitching to an investor audience on a demo day. It was a proud achievement for me as a Head Sherpa to see that 70% of the participant startups got high interest from at least one investor 🙂


Some of my most memorable experiences included helping a naive young engineer-turned founder to revisit his product from scratch, helping a promising pair of founders identify an interesting pivot, helping a shy founder take his first steps towards a more effective sales pitch and go-to-market strategy, helping an innovative startup address their sustainable differentiation in the market, helping a travel startup with tons of potential customer contacts, and helping a founder completely turn around their pitch deck at 2am on the night before the demo day!

Personal journey: Learnings for own venture

One of my biggest takeaways from the fellowship was objectivity. Working with these founders and helping them think about their problems helped me look at my own venture objectively. I realised I had made so many assumptions and taken so many decisions as founder in isolation, which I would have done differently given what I know now. I also got introduced to a lot of new concepts in various industries and was able to cross-pollinate some of those insights with my own thoughts, giving me new ideas about my own area of work. Moreover, evaluating every startup in my cohort using the Critical Success Elements framework also helped me realise where my own startup was lacking in its attractiveness as a bet for a potential investor.

Life after the fellowship

Exit options are great for a fellow, if you ask me. First of all, at least 2 startups in my cohort showed interest in hiring me, and so did the incubator that I worked with. Moreover, I was able to build relationships with a bunch of very smart and passionate founders, some of whom have become sounding boards to exchange thoughts and ideas. I got to work first-hand with some established founders, who we engaged as mentors for my cohort. I also made a lot of friends in the VC industry and saw some doors of opportunity open through this network. Always helps to know someone in a fund when you’re thinking of approaching them for investment. I’m anticipating that future Head Sherpa fellows will be recruited in cohorts, and will find other fellows in their cohorts evolve into valuable connections for life 🙂

In conclusion, the Head Sherpa Fellowship was a life-changing experience for me, and I hope future Sherpas will derive similar value from it. I look forward to seeing this grow into a program as reputed and aspirational as Teach for India and the Young India Fellowship!

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