“*You have to trust in something: your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well-worn path. And that will make all the difference.”* - Steve job’s Stay foolish , stay hungry speech I urge you to [read](https://stevejobsarchive.com/exhibits/stay-hungry-stay-foolish) the process of writing this commencement speech that Jobs embarked on during the final weeks before delivering this iconic speech which has more than 120 million views. He was anxious because it was his first time talking to young 22 year olds graduating college. He knew he had to use his life and its stories which he refrained from doing elsewhere.^[I believe this is one strong reason why this speech gained its resonance as well] I want to indulge in a similar endeavour with this post. I will connect the dots of my career so far in the hope that it resonates with you the reader. ## First taste of blood Steve’s commencement talk had an impact on me when I was a young 20 year old thinking about my life’s purpose with respect to work. My college and the course I chose were not engaging me anymore as I entered my final year. I was coasting through the coursework and bidding my time to get out and make my mark on the world. The hunger to build something of my own started forming due to my interest in startups and my disinterest in coursework. Me and my friend started a VB bulletin based un-official college forum. We wanted discourse and information sharing to happen between students via college wifi. It wasn’t a novel or unique idea, we saw that our neighbouring campus of IIT-Chennai had a LAN network which everyone used for sharing notes, games and movies. We had college wifi but no digital forum where people could do the community sharing. This was in 2013-2014 when Facebook was just coming about in India. There was no concept of community building that was prevalent. We ran it for good 5 months before it was blocked by our college’s IT team. We had few users outside of our friend’s circle using it for various purposes. I was the non-engineer working on pitching the tool to early users, acting as a moderator and community person trying encourage communication. Once we got shut down, I culminated this phase by conducting a startup pitching workshop for our college fest. It was probably the first of its kind for our college where I got people from industry to come in and be the judges. I remember cold emailing folks in the industry who I followed and requesting if they would like to part of this workshop. One of them, Raghu Mohan who was a journalist covering startups in India said yes.^[Startups were nascent space back then in India. Yourstory where Raghu worked was the only homegrown media entity covering startup space in India. I applied for a role over there but they would have read my email and decided to not let any reader interact with my horrid writing] Starting the forum and organising the workshop opened my eyes to world of entrepreneurship. It also made me believe that anyone, including me could become an entrepreneur. ## Fixating on the idea and scratching your itch After completing my college, I stayed longer than required to clear my exams in Chennai. During this time, I had difficulty finding an apartment to rent. The stigma of being male bachelor and wanting to rent a flat was too much for landlords in Chennai^[This problem is still prevalent in all metros in India. For a country with more than 70% population younger than 30 years , we don’t have housing for them. ]. I ended up staying up with few friends in my neighbouring college, IIT- Chennai. The house also happened to be their office for starting up. Two smart chaps going about building a blue collar services marketplace similar to now famous Urban company^[They were looking to build for plumbing, house helps and other categories which Urban company didn’t start yet]. Urban company was still a startup in late 2015(s). Through osmosis I started to think about building my own startup, a version of renting marketplace that would allow bachelors like me to find an apartment. In addition, they could also rent the furniture as and when required. This would allow bachelor’s to rent affordable housing with furniture that suits their needs. The startup lasted only on paper unlike my roommates who at least had an app and some beta users. But both our startups never went beyond the initial phase. I never mention this experience publicly but wanted to use this to cite why idea alone is enough. I held it too close to my heart, shared with few folks and when it didn’t elicit any interests, committing to it became even harder and the easier option was to chalk it as a startup idea and move on. In order to build a startup, making progress and putting it in the hands of customers is the highest leverage work. The second lesson was it was an operation heavy business that couldn’t kick-off without investment and I had no credibility in the market for anyone to take note. The idea came from scratching my own itch but the world view as a young person is very limited. Building non-digital consumer marketplaces should have been a non-starter because where I come from. I didn’t have an answer to “what makes me believable in the market?”. But being in that house with my roommates taught me a lot about building apps. If that didn’t happen, I would never have the conviction to think that if the idea and business are solid, building an application for it wouldn’t be too hard. ## Hard problems attract but addressing diminishes our odds Circa 2016, first job was going great. Learning new things every week and building software that has a real life impact. Sifting through tons fo reading and upskilling self to be a product designer. My CEO takes interest in an idea I pitched to her and says go ahead and build it. I get excited about solving Urban commuting in Hyderabad. I band my school friends together and start drafting all sorts of plans. The current version of [Namma Yatri ](https://nammayatri.in/)is what we envisioned back then starting with a bus network interoperable with the upcoming metro and autos for last mile connectivity. 1 year of our efforts went into making it a reality. We even ran a pilot with the government but then Demonetisation happened and they decided that digital money collection is their top priority not our app. We were shut out instantly without a say in it. The hardest lesson I learnt is to never build for 1 customer and call it a startup. It was an extension of the services company where the project got shut down and we just move to the next one. But for me it was not that simple. I decided to never build anything relying on government approvals. It also taught me how friendship doesn’t translate into working relationship. One needs to evaluate the capability of other co-founders before banding together. We didn’t have many complementary skillsets and much overlap which strained our relationship severely by the end of the stint. I did move on to the next project but eventually quit to do things on my own as product designer^[The project I moved to was blockchain. I was one of the bitcoin maxim bros for a brief period. Blockchain for trade sounded like a perfect fit until I realised trust is not people say but what they do. Its a story for an another time]. ## Stumbling into founding a venture I have [[Stumbling into founding a venture|written]] about this at length. One interaction with a client led to an idea that has no relevance to me, agri- logistics. 1 year later through a cold outreach to agri-leader, I entered the space of produce logistics. > I am a big believer of cold emailing and reaching out to interesting strangers on the internet. I have written to multiple people in the past. Our company’s existence happens to be one such shining example of outreach turning into an opportunity. > > I am an avid listener of podcasts and was listening to the Amit Varma’s “The Seen and the Unseen” podcast. An [episode](https://seenunseen.in/episodes/2018/9/16/episode-86-the-state-of-our-farmers/)which dropped on 16-september-2018 was in Hindi. It happens to be the only episode in Hindi. The guest was [Mr. Gunvant Patil](https://twitter.com/gunvantpatilh)of Shetkari Sanghatana (SS) . After ramping up across 3 regions, we had to abruptly wind down. We ran the startup for a span of 2 and half years and exited through an acqui-hire. I corrected all my previous mistakes but made many newer ones in the process. My biggest takeaway was importance of narrative framing and building in public. Second takeaway was speed is of essence. More than progress, momentum does a better job of moving things forward in the 0-1 and 1-10 phases of the startup. Third and final one is put in the reps and iterate faster to minimise the moving parts. Those three lessons were due to failure as a founder but I invested 2 and half years of my life and didn’t let up. And it made all the difference. ## Setting sails for a different region The common theme across all these startups experiences is my fixation with domains that are [[Legacy domains|legacy]] in nature. > Legacy domains imbibe this nature of resisting change through front line workforce. These domains are hard to transform and take a lot of effort in making an impact. While coasting as an operator and writing a newsletter regularly at the startup that acquired us, I came across writings of a log-tech tinkerer who wrote a 4 part narrative essay documenting about platform building in logistics . I read all 4 and instantly felt seen. I [reached](https://www.linkedin.com/posts/jonahmcintire_what-i-like-to-do-on-a-week-off-is-to-write-activity-6983808655531868160-S7ja) out to him on the socials and referred to some of my own writing. Post startup , I decided to write everything I learnt. So, I had a few of my own to share. He responded and we started talking. Over the next 6 months, I sought time and showed up with topics to discuss. It was like finding a fellow nerd who is also a mentor. After gaining some comfort, I hinted at the idea that I was open to work with him if an opportunity presents. Few months later through an another bout of serendipitous set of events, his organisation had an opening that they needed to fill quickly and he wanted to check if I would interested. I said heck yeah and after due process I joined them 2 and half years ago. My job entails contributing to the work he published which started off our conversation. ## Did the dots connect? What do you think ? The underlying theme across all these experiences is desire to find contrarian stances. It started with trying to build a consumer marketplace when I was too young or focusing on fixing urban commuting which was under government’s purview. Work needs to be more than what it seems, it needs to be where I play and exercise my creative juices. I read business literature as a recreational activity. All of these are fun to me and I want my work to feel like play when delivering outcomes. There is less than 1% probability that I would end up at my current role from where I started. Yet, penning this down makes it sound like a reasonable career progression. “Which other approach would have made sense?”, might be lingering in your mind, it certainly does for me. As I am contemplating my next step in the current organisation, I was asking a senior what should I do next. He is a veteran who has 30 more years of experience in this domain - “Don’t plan, just enjoy the next opportunity which comes your way”. I felt like he was sharing a secret that is too obvious but true. I lucked out by following his advice by being completely unaware. I wrote this post to substantiate to myself that I have been doing this from the very beginning and here is a person I respect offering the same advice. My gut told me I need a change and I listened to it and applied for a change. As of Nov 1st, 2025 I am still uncertain whether it will go through but I stuck to my pattern of following my instinct in the process of building a career and let serendipity do its bit. Never sure where I will end up but confident that I would be able to connect the dots backwards. **** `First published`: 02-11-25 #personal #career