10 lessons from failing in my startup

My journey of building a startup during my sophomore year, how the experience changed me and the lessons I learned

Aman Dalmia
8 min readFeb 22, 2020


The logo for ScholarMate: our idea to create a platform for bringing together teachers, parents and students.

When Jeff Bezos was stuck at the decision on whether to start Amazon, he introduced the idea of the regret minimization framework. It goes like this:

I wanted to project myself forward to age 80 and say, ‘Okay, now I’m looking back on my life. I want to have minimized the number of regrets I have. I knew that when I was 80, I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a huge deal. I knew that if I failed, I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried. I knew that that would haunt me every day, and so when I thought about it that way it was an incredibly easy decision.

Although I encountered this specific term only recently, this is the mantra I have always adopted throughout my college life and still do every day. It’s incredible how it makes every decision so much easier. Hence, when faced with the choice of whether to work on building a startup when I was a sophomore, the answer was obvious: I would surely regret not trying this. A few of my close friends and I came up with the idea of building a unified platform for teachers, students and parents, during the Code.Fun.Do hackathon organized by Microsoft in October 2015. The motivation for me was to build something of my own to help people, along with my close friends. We eventually stumbled on a name we were satisfied with — ScholarMate.

The first mockup of our website

Instead of reading success stories, I read a ton of startup failure stories, to avoid making the same mistakes that many startups have already made. The big lesson was, validate that the need you are trying to address is real and whether your idea solves that need before building anything or spending a buttload of money. The good thing was, a significant chunk of money spent by startups is taken up by hiring and getting office space. We did not need to do any of those: we had 3 developers, 1 marketing person,1 designer and our hostel rooms.

So, we made a list of all the schools in Guwahati and set out to talk to the Principal of each school and the parents that would roam around while dropping off/picking up their child. Every day we used to shortlist the schools to visit that day, distribute them amongst us, and head out to the city (which was about an hour away) every morning. The idea was to randomly enter the school and go straight to talk to the Principal. It was not as straightforward as we had hoped everywhere, we had to pull some strings to just get into the school premises, but once we got in, the Principals were mostly excited about the idea and supportive of us. Finally, we got a chance to have our app demonstrated to parents during the parent-teacher meeting in one remotely located school. The only problem was that we had 3 days to build the app when we only had a barely working prototype. We decided the opportunity was worth it and coded for 3 days straight with hardly 5–10 hours of sleep in total. But we had a demo. When we showed it to the parents, we got great testimonials already. The Principal was so happy that he decided to start the next academic session using our app. That was big. We were actually going to operate in a school. We were extremely excited.

Sneak peek into the initial screens we had in our app (I still love them)

However, that exercise brought us face-to-face with the real challenges of building a product for the kind of audience we were facing — neither the parents nor the school were tech-savvy. So, any communication with the parents happened only in-person or through the medium of paper. One example of how this impacted us was the distribution of usernames and passwords for each child. We had to print out the details for each student on a separate sheet of paper, hand them over to each child individually during school hours and ensure, as much as possible, that after school the parent takes out that sheet and logs in to the app.

There were many other implementation challenges, but the biggest mistake this exercise highlighted in our user study was that we never talked to teachers. Hence, the incentive mechanisms in place were only for the Principal and the parents. For the teachers, it was just additional work, and soon, they lost interest and motivation to use the app to enter information like attendance or homework. Another major factor that came into play was our academics. We spent the whole day either in the city talking to our end users, or building the app or making the business plan. More often than not, I got to see the professor teaching a course only during the semester exam.

An early version of our B-plan that we pitched in various competitions (and came 2nd in one)

After that semester got over, we took some time off to reflect on our journey over the past few months. Although there were several product challenges, the biggest hurdle was the academics, and we realized we can’t do both of them. Quitting college was not an option for us, and hence, we decided to not continue further. This was a difficult decision to make as this startup had become very close to our heart, having invested our heart and soul into it. Also, the implication that we won’t be working on something that we started, and instead would work for someone else, was not easy to accept at first. I think that is also a reason that this retrospective took so much time before I was comfortable talking about it.

The main takeaways from this experience were the lessons I learned which are always going to stay with me as my North Star, guiding me wherever I am, whatever I do:

  • People are everything. Hire very carefully, and once hired, care for them relentlessly.
  • Always keep the vision in mind and keep reminding everyone the same.
  • The process is essential, not boring. Keep track of everything you intend to do and have weekly check-ins to ensure you are making progress, identify blockers, work on them, repeat.
  • To build something from scratch, you need truly motivated people who are ignited with passion towards the same goal. There will always be naysayers. The important thing is to focus on the YAY-sayers and draw your energy from them.
  • If you are building something of value to other people and put your heart into it, one day, you will receive it back. That day will make it all worth it.
  • Build meaningful relationships with people you work with, understand what motivates them, appreciate them, support them, and, when needed, give them feedback to help them grow.
  • Don’t be afraid of failing. Always think in terms of the regret minimization framework: Will I regret not doing this when I am 80 years old?
  • Develop a habit of extreme ownership of anything and everything you care about. Drive it end-to-end.
  • Don’t let anyone tell you what you should do. Let them help you, hear them out, think through carefully, but never let anyone make the decisions for you, even though sometimes you might want them to.
  • Work on something you love. Anything else is probably not worth it.
Left: Receiving the second prize in the B-plan competition by Startup Assam. Right: day 1 of code.fun.do which led us to the idea that became ScholarMate.

Looking back, this experience changed me profoundly as a person: who I was, what I valued, what I knew was possible, what I wanted for myself and my belief about what I could become. Earlier, I couldn’t speak to strangers, the thought of giving a presentation scared me to my spine and puke in anxiety, I considered myself useless and thought I could never achieve anything in life. This experience made me confident about not only my speaking and communication skills but also on my ability to make a difference in the world. Being forced to talk to strangers to make the idea a reality drove me way out of my comfort zone. It made me believe that I matter and if I put my energy into something, I can make it happen, however unlikely it may seem to anyone. There were so many people whom I am grateful to have been a part of this journey: my co-founders and team members (Raunak Agarwal, Prabal Jain, Ankit Chahar, Roopal Gupta, Umang Pardhi), mentors and friends. I am especially thankful to other entrepreneurs for having valuable conversations, hearing our crazy ideas, giving critical feedback, providing reality checks and inspiring us when we needed it the most. My best friend, Prabal, played a massive role in my journey, and I can never be grateful enough for his support.

Now is the time to take risks. As you get older, your obligations increase. Once you have a family, you start taking risks, not just for yourself but for your family as well. It gets much harder to do things that might not work out. So, now is the time to do that. So, I would encourage you to take risks now, do something bold.
- Elon Musk @ USC Commencement Speech

If there’s anything that you might want to share with me or give me any feedback on my writing/thoughts, I would love to hear it from you. Feel free to connect with me on Twitter, LinkedIn or follow me on Github. To stay updated with my posts, do follow me on Medium.

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Aman Dalmia

Curious about almost everything. Passionate about climate change and education. Trying to be helpful!