“Punching in travel bills was a painful process. I just wanted to solve it”. Sivaramakrishnan Narayanan is a person who wished to create a change. He saw an opportunity in spend management, left the safety of a job, and pursued his dream of starting up.
When his personal pain point became his entrepreneurial idea, Fyle – Intelligent Expense Management Software, took wings.
Let us read through his inspiring journey on building his dream and being successful!
YC: Childhood is a period where people shape themselves. Would you like to walk down memory lane?
Siva: I was born in Chennai. We shifted to Delhi for three years but then moved back. I have an older sister. My mother is a homemaker. My father used to work for CMC Limited. He was a part of the team that computerised the railway reservation system for the first time.
He then switched to the private sector and started a services company called BITECH. I was very young to understand what he was doing. Dad once bought me a dolphin microcomputer. I viewed it as a video game, but it wasn’t. He encouraged me to try these things. I thus had exposure to programming and other such activities early on, which was rare.
YC: What was the journey to BITS like?
Siva: In 12th class when I joined back to school after summer, everybody was talking about IITs. I was not aware of IITs and had no plans of preparing or joining them. Most of my classmates were going for the IIT coaching, so I joined too. I didn’t enjoy the coaching at all. So I dropped out of it and focused on my 12th grade instead.
I scored quite well in my exams. A friend asked me to apply for BITS. Those days BITS selection was based on academic performance unlike now. I read about BITS and found it interesting. My parents wanted me to find something closer to our hometown. But my sister encouraged me to go for it and thus I joined Birla Institute of Technology and Science, Pilani – Computer Science.

@ BITS
YC: How were your engineering days
Siva: BITS had people from all across India. None of us had ever lived by ourselves till then. So we learned a lot about becoming independent. Trying out new things, becoming independent and facing new challenges were the biggest learnings from BITS apart from academics.
During those times most of the tech development work was done outside India. Though I did an internship in my second year, it was not worth it. At the end of the fourth year, I went to Motorola. Again, it didn’t go well, but I ended up building something out of sheer boredom.
Chat App
I built a little chat messenger for all the interns to chat with each other. It was a little clone of Yahoo Messenger where people could just ping each other and chat. I enjoyed building it and felt good seeing people use it.
After college, there were no exciting job opportunities. I knew that to learn something meaningful and challenging I will have to go to the motherships in the USA. So I decided to do a PhD in Computer Science and joined The Ohio State University.
YC: What were the major takeaways for the life ahead from the six years in Ohio?
Siva: Things that I did back then, I apply even now.
1. One of them was doing Research. Whatever you do, a ton of people come ahead of you. It’s useful to take a step back and understand what has been done, and what the state of the art is, before doing something. It has been ingrained in me since then, to take some time to understand the field before taking the plunge.
2. Another was Evaluation Research. Professors across the world will look at your paper and will tear it to shreds. This brutal feedback too helped develop a mental toughness towards negative feedback.3. To take hits. My friends were settling in life during then, and I was doing homework. I learned to see it from a different perspective. I was giving up much, but it would certainly pay off. I developed a conviction to build for the future.

@ The Ohio State University
YC: Why a startup? What were the initial days like?
Siva: 2008, when I completed my PhD, was a terrible time to look for a job. A friend suggested moving to California. It was then that Greenplum, a big data company came by. The intensity of the work matched my expertise, I found it very interesting and decided to join them.
Learnings at Greenplum:
Greenplum was a typical tech startup. I picked up a few good learnings, which help me even now at Fyle:
1. Interaction with the support team is a MUST – I used to talk to everybody in the startup to understand what each one of them was doing in detail, especially the support function. This gave me a very good understanding of customer orientation.
2. Learn from your own mistakes – I was the youngest in my team. So even if I made mistakes, people would be accommodating. This also helped me to engage with things confidently.
YC: What made you switch from Greenplum?
Siva: Greenplum was acquired by EMC, the switch was part of the acquisition. I moved to Bangalore, and I continued working there for about seven months. After an acquisition, things slow down generally. This journey had somewhere planted the seeds to start up within me.
When I joined Greenplum, there was already a product and paying customers. I didn’t know what it meant to get your first customer. So I decided to join an early-stage startup, to get accustomed to the initial phase of a startup. Qubole was a good opportunity, hence I joined.
YC: What was the journey in Qubole like?
Siva: 4 major takeaways from Qubole were:
1. Learning Hiring
2. Mentoring and guiding a team
3. Meeting my co-founder
4. How to build a great team
Hiring – One of the first things I learned at Qubole was hiring. I remember one of the folks I interviewed asking me, “Qubole is a startup, is it risky for me to join?” I blurted out something at the moment which I have used forever. I asked him “What is the risk? You’re early on in your career? Let’s say you join this company and it falls in six months, you think you will not be able to find a job? I told him working at a startup will give real-life experience and will definitely make him more employable! That was the first time I convinced somebody to take a plunge. I grew confident in my abilities.
While interviewing new people, I found something interesting. The young minds got through our interview bars. What they didn’t have on the resume was the experience. They hadn’t shipped a product, they didn’t have the opportunity to do it. This was a contrast from my Greenplum experience where I worked primarily with experienced folks.
Mentorship – At Qubole, the team was relatively young. One of my key roles was to mentor them. It was a significant change from my previous job at Greenplum. Although it was quite challenging, I was able to learn a lot.
Co-founder – I knew Yash for many years prior, but we worked together at Qubole. He was in sales. We used to travel together to meet customers.
Great Team – I learned a lot from my bosses at Qubole, Joydeep Sen Sarma and Ashish Thusoo. The art of dealing with people and at the same time how to be fair. Qubole had a great working culture, seeing Qubole built was really helpful at Fyle.
YC: How did you choose between B2B and B2C?
Siva: Although Yash (my co-founder at Fyle) was in sales and I was on the engineering side, we had to often travel together to meet customers. We faced great difficulty in arranging the bills and entering data into forms for reimbursements. Our initial discussions took place during that time. We talked to a lot of our friends in other companies and could see the need. I did a prototype using Gmail, to solve this problem. It was neat and many liked it. That was quite encouraging.
Both of us were interested in starting something of our own. We evaluated seriously whether to go B2B or B2C. But we realised neither of us had the B2C DNA. I built enterprise software and Yash sells enterprise software.
Both of us were used to a world where an interested customer evaluates your software, buys it, and pays for it. B2C was very different. I didn’t know how to make it into a business, there was no founder market fit! Thus we chose B2B.
YC: Any specific reason that you thought of expense management software?
Siva: It started with a personal pain point because both of us had faced it. We spoke to a lot of others, and everybody hated the problem. So we did some research. There were a few players, but the solutions out there were not particularly employee-friendly. It seemed like a massive market.
For building Fyle, we took the B2C apps as an inspiration. Using a B2C is simple and convenient, unlike enterprise products. There is no manual or guidelines for using a B2C product. You download it, you figure out how to use it. We saw this as a huge opportunity. The idea was to bring B2B with the B2C interface approach to clients, to simplify things.
YC: Can we talk about the sales and marketing journey for Fyle?
Siva: Sure, I would like to break this into two parts – In India and in the US.
India – Our first customer was Qubole itself. The initial customers were also from our network in India. Both Yash and I reached out to our primary and secondary networks. It snowballed and we found a good market to grow and sustain in India.
But we took a strategic call to focus on the global market. It meant everything changed about sales and marketing, even the product.
Adaptations …
US – The B2B market in the USA is humongous as well as organised. They use cards heavily, and the bar is also very different. They also typically use a lot of other purpose-built software. So your software has to work with the others. All that meant, we had to do a bunch of work on the product side.
Our sales and marketing also had to change. The US market is so huge, that you should go narrower. Your customers should look similar. Having customers from similar backgrounds helps you land more customers from the same. For example, if a real estate firm seeks out your product, and finds other real estate firms using your product, they will be tempted to buy it.
Marketing – It depends on the segment. If you’re going for the SMBs, inbound marketing works very well. Make sure that you’re in the consideration set that shows up on Google search. It takes time, but SEO is one thing that I would say to invest in very early on. At Fyle we started with Google ads because we didn’t have SEO. We didn’t have the content. Google ads were like steroids. You require it at times, but you can’t inject too many.

@ Team Fyle
YC: What is the right time to raise funds? What should one be careful while going for funding?
Siva: Funding is like fuel. You don’t necessarily understand all the ramifications of funding early on. It comes with a few strings attached, but raising funding is worth it. You have to give yourself enough chances. If you’re cash strapped, you’ve got fewer shots at success.
Funding gives you a cushion. You will be able to plan better, and it gives you a few additional chances. Also with Angel investors, you would get additional guidance. You get a set of people you can lean on, and Angel rounds don’t take very long either.
YC: What keeps you going? What would you suggest to the upcoming entrepreneur community?
Siva: I would very strongly recommend financial security. Figure out how you can go for two years without a salary. That question is very important because it will free you to a great extent.
Secondly, hire great people, give them opportunities to do wonderful things. Build their resumes so that other people want to poach them. That means you’re doing a good job, which is giving people ample opportunities to grow. Then, manage to retain them. It’s a wonderful problem to have. Entrepreneurship is a never-ending set of challenges. You’re not going to have many boring days.
YC: Technology is ever-changing. How do you keep yourself updated?
Siva: Three things that help me to keep myself updated are:
1. Twitter – A great place to be, for tech and in general. I find things that spark a bunch of learning.
2. Side projects – I build prototypes from time to time. I like the whole process of figuring out, coding and shipping the prototype.
3. My team. They will mention something new in the meetings, and I’ll have no clue what they’re talking about. I will frantically read about it. They keep me on my toes.
YC: Somebody whom you would like to thank on this journey?
Family Forever!
Siva: Apart from Yash, who has been a great partner in the journey, I’d like to call out the support from my family. My wife Sushmita is one of the reasons I’m still going strong. We started up just six months after our twins were born. It would’ve been easy for her to ask me to stay at my job. But she was super supportive. She gave me the security to say to myself, “Okay, Let me mess around for a few years and see what happens”. My mother-in-law and my parents have also been super supportive.
I would also like to thank my kids. They don’t allow you to compromise yourself. Children don’t care if you had a bad meeting or a terrible day. They want your undivided attention when they come to you, which is fantastic. It forces you to switch off for a bit. That little happiness is indescribable!”

@ Family
It was a pleasure talking to you. Your journey is no less than inspiring, and we wish you the very best in future.
Thank You!
Interviewer: Divya Jain