Ishan Rakshit, Co-Founder, Shopflo – Interview on Creating the Future of Checkout.

Meet Ishan, busy building a Checkout Infrastructure Platform for D2C brands globally @ Shopflo.

Ishan describes himself as “Someone who does not shy away from hustle + Giving those extra hours doesn’t come up as a hiccup for me + A fun person to hang out with!”

Let us read through his fantastic story… 

YC – Ishan, welcome to Yellow Chapter. The idea of the interview is to know you as a person. We will start with your childhood memories, college days, and professional roadmap and eventually will talk about your startup. So, can we start from the very beginning?

Ishan – Sure. So I was born in Patna, a City in Bihar, where I spent a few early years of my childhood. We then moved to Ranchi, City in Jharkhand. I have spent the majority of my school life in Ranchi.

My dad used to work with SBI. Because of the transferable nature of the job, we got to see him lesser than we would have liked. But my parents prioritized quality education for me and my sister over anything else and kept us stationed in Ranchi and kept shuttling in and out himself. 

My father is the most practical and pragmatic person in the family. He had done his Bachelor’s and Master’s degrees from Banaras Hindu University and Jawaharlal Nehru University respectively. After trying his hands in civil services, professorship etc., he ultimately ended up choosing the bank life.

My mom, on the other hand, has done her Bachelor’s and Master’s in Science (botany) and then also an MBA. But then we happened after marriage. She took that hard call of putting her career behind and caring for us. She has even done a B.Ed to kick off her teaching career. There was this strong push for education from both sides and that came with real sacrifices from their end. 

@ Family

My elder sister – Dr. Vinci Priyasha, is almost a year older than me. She has recently completed her M.S. ENT from GMC, Chandigarh and is now working in Delhi. Throughout my life, she has been my strongest supporter and I have always looked up to her for advice & guidance – and continue to do so. 

Back in school, I was equally active in sports as well. Ranchi had an exciting football culture. There were localities with large accessible football grounds and it was something I always looked forward to after school. ⚽⚽

@ Football

Why Engineering…

For the longest time, I had been super fascinated by theoretical physics. Super enthusiastic about math as well. This led to my excitement about going deeper into astrophysics. I wanted to get into research. So I prepared, took my SATs, and was almost going to pursue my Bachelor’s in the US. But due to financial limitations among others, I decided not to pursue it.

I switched gears and start preparing more seriously for Indian entrances. The plan was to get into aerospace engineering & then figure out a way to pursue research in the US after my Bachelor’s.

2012 – I got through Indian Institute of Technology, Bombay – (M.Tech.), Aerospace, Aeronautical and Astronautical Engineering. 

Day one – engineering was never a conscious choice. It was a gateway to pursuing sciences abroad.

YC – How was engineering, and what were the learnings? Many engineering students read my blog; they find these stories inspirational and relatable. What would you suggest to them? How can they make the best of their college days?

Ishan – 2012 – 2017, I joined IIT Bombay to pursue Aerospace Engineering. I started loving the college as there were so many things apart from academics to enjoy and learn from. IIT started opening my eyes to things that I did not know. 

Early on, I got exposed to Pratham – Student Satellite Program, a microsatellite that ISRO was supposed to launch. And it was mindblowing to know that people as young as us can play a part in putting something out in outer space. In 2016, the satellite was finally launched. 

In my third year, I became the Concerts Head at Mood Indigo – one of the largest college cultural festivals which happens on a massive scale. The most significant learning along the way was if there is an inspiring vision out there and the drive to make it happen, people don’t care about where you’re coming from. And if you have enough ownership, you’ll figure out a way to do it.

@ Mood Indigo

At the end of my third year, I, with three of my friends (Rishabh Bohara | Rakshit Jain | Suyog Wankhede) and started a company – Kibo.

Problem – The idea behind Kibo came from failure of crowdfunding models in India; people like you and I don’t keep on donating to online campaigns because either we don’t have the trust in the platform, the cause, or we don’t end up seeing the end of it. 

Solution – We decided to create an ecosystem where we make it a habit for people to donate. We ran a few pilots with brands, campaigns and NGOs to make cause marketing campaigns work successfully. Over time, we realized there were multiple issues with the way we were approaching the solution & decided to shut it down. Kibo being a failure meant that drive needs so much more to go along with it to really move things. 

Reason for Kibo’s failure:

1. Lack of business acumen – we did not spend the money we had available with us to scale. 

2. Not the right team – we created a team of college students. We never rose above our levels and hired full-time folks with experience.

3. The model itself didn’t have a strong defensible moat, so a natural fizzling was destined to happen.

Suggestions …

Just one – Get your hands dirty – do projects | take responsibilities | organize events | If you want to start up, go ahead.  

You might fail and fail, but you will know whether you enjoyed the journey or not. Until you try, you’re constraining your options by what you have experienced versus what you might like.

College is an excellent breeding ground to try and explore. Your currency in college is your enthusiasm; make the most of it! 🏆🏆 

@ IIT-Mumbai

YC – I would like to talk about your professional roadmap and learning.

Ishan – I sat for college placements soon after. Like most college placements, you do not get to choose your first company; the company chooses you. 

July 2017 – I started my career as an Analyst @ MSCI. Joining companies in aerospace was out of the question – significantly less pay, and work not being that exciting were the primary reasons.

By now, I knew I had tasted blood & I had to start up again and this time I had to get it right. What was important was to ensure I had a financial cushion while I did that.  

MSCI is a great company. My boss Neeraj Patodi was super helpful and a great mentor. I really enjoyed working with the entire team of eight people I used to work closely with and learned a lot from them about building software at an enterprise scale, working with cross-border teams etc. 

July 2018 – Despite that, I wanted to move towards more business-facing roles and I joined EY-Parthenon as an Associate Consultant. In between my jobs, I played around with a couple of startup ideas: 1) giving access to high-rated premium doctors through teleconsultation, and 2) Assisted Learning platform for Early Years, similar to Osmo

But in both cases, something or the other didn’t work out. So scrapped all plans and decided to work closely with startup founders. Either I operate or invest. Learn what works and what does not. 

Jan 2020 – Investment Professional @ Elevation Capital. I was looking at early-stage investments in Fintech-SaaS primarily. I’ve worked very closely with Mridul Arora, and Vasudha Wadhera. There were immense learnings that I picked from both of them. 

1. Think fast, work faster – A very fast-paced environment because the startup you want to fund is getting funding from other VCs. 

2. Research is key – Stakes are quite high, so you have to know the space really, really well. 

3. Surrounding yourself with great people and aligning them to the same goal leads to great outcomes.

YC – How did Shopflo happen?

Ishan – May 2021 – I decided to put on my paper. Nothing was in place, neither the idea nor the team. But I knew if I did not quit, I would not be able to give my heart to it. 

While serving my notice period, I spoke to 100+ folks in my network and second-degree connection who are remotely thinking about starting up. This time I need to make the idea work. 

I did not have very strong filters around the idea or the sector. I knew I just needed to build a solid co-founding team and was able to do so with Ranjan and Ankit. We knew we were all excited to solve for the same customer.

July to November 2021 – All we did was sit with brands, overheard conversations, and talk to their teams – marketing, tech, growth, logistics etc. We went deep into problems that they were facing across verticals like inventory management, omnichannel marketing, discovery, payments, reviews, user experience etc.

It seemed like dropoff at checkout was the most common problem & one which hurt all brands badly. We decided to create a checkout platform for e-commerce. We could see the promising growth for D2C brands that India was showing. Hence – Shopflo – the fastest and smoothest checkout experience, was born.

@ Team Shopflo

YC – Can we talk about some numbers of Shopflo and competition?  

Ishan – Looking at India’s e-commerce, $5 billion would be D2C brands + an additional $5 billion coming from small marketplaces, apps, etc. Amazon and Flipkart would be around 60 – 70% of the market. The remaining is what we are focusing on. It’s a high-growth market with 20% plus year-on-year growth. We do feel that there is a 100x market outside India as well. 

We have quite a few brands live on Shopflo and are growing fast. Checkout conversion is one metric that we track very closely. With few merchants who have spent more than one month with us, we have been able to create more than a 10-15% conversion delta, which is a direct impact on their bottom line. 

Pivots, if any – No, many hypotheses have been positively validated. We have a very clear understanding of what we’re going to do in the next two years.

YC – What is your take on marketing and sales? And suggestions for fellow founders?

Ishan – We’re not still an authority there, to be honest. But based on my experience, we have realized marketing in SaaS is a lot about relationship building – with customers & prospects alike. We’re investing a lot in content around the D2C shopping experience – A2Z of D2C


1. There is more value in setting up a great team versus obsessing over an idea first. Regardless of how desperate we are on bandwidth issues, we will never make compromises on hiring. 

2. Building quick and dirty is key in an MVP stage. We released our pilot within 2-3 months of building. Within 4 months, we had released a full-fledged product. Loss of time = Loss of learning!

4. A lot of things, founders, ideally should front load themselves for the longest time. Customer success is something we spend a lot of time on – that’s where we get the best learnings from. Nothing in a competitive market is your moat except your insights. 

YC – What keeps Ishan going? 

Ishan – This is a tough one. I never thought about it, to be honest. Put an exciting problem, great ownership and epic people around me & life’s just happy. Trying to start something of my own since 2015, and I have really just tried solving for the same. 

YC – Ishan, I genuinely believe many people contribute to where we are in life. They are our family, friends, teachers, mentors etc. People you would like to thank in your journey so far?

Ishan – Too early for that! But a major part of this has been my partner in life Deepshikha Singh who I got married earlier this year. 

Ishan it was a great conversation. Thank you for your time. Yellow Chapter wishes you all the very best in your future journey.

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