Freshworks founder Girish Mathrubootham on going 'All In': IIT-IIM and big-city background not crucial to start-up success

Freshworks founder Girish Mathrubootham's memoir, 'All In', was released earlier this year. (File image)

Girish Mathrubootham’s Freshworks became the first Indian software-as-a-service (SaaS) platform to list on Nasdaq. In 2021, the company raised over a billion dollars in its initial public offering (IPO), and recorded a market cap in excess of USD 10 billion. Yet, Mathrubootham hadn’t charted the most obvious—or even most straightforward—route to start-up success.

He wasn’t born rich. He wasn’t even born in a big metro. Nor did he go to an Ivy-league college, where he could make the kinds of connections that could translate into introductions to investors and mentors later on. In his memoir, 'All In', co-written with journalist Pankaj Mishra, Mathrubootham Girish writes of this time: "Looking back, those years were an incredible training ground—a mix of failures and breakthroughs that shaped my identity."

Over a video call, Mathrubootham said that he agreed to co-write his memoir - All In - with journalist Pankaj Mishra, precisely because he didn't go to an ivy-league college or have the kind of connections and family money that might have given him a leg-up in the start-up world—in the hope that his story could serve as a springboard for others like him, those from tier 2 towns or non-ivy-league schools. A kind of 'Hey, (if) this guy can do it, I can do it too.'

Edited excerpt from the conversation where he also talked about the impact of US tariffs on business and why SaaS companies will need to change in the near future:

In 'All In', co-authored with technology writer Pankaj Mishra, you talk at some length about your early life—parents' divorce, struggles at home, moving to Chennai and discovering movies like Qayamat Se Qayamat Tak, and how you discovered coding and fell in love with it. Now, these experiences – both personal as well as professional experiences – are very specific to you. What, if anything, do you think other founders or people starting out in their careers could take away from your autobiography? Also, when you were writing the book, did you have a particular reader in mind?

The whole reason for spending time and deciding to write the book was a conversation that I had with my co-author Pankaj, where his point was based on his interactions with various founders. He felt that, in general, there is a myth around entrepreneurship—that successful startup founders are all Ivy League-educated. If you have to get funding, you have to be from IIT-IIM or Stanford-Harvard, because the VCs (venture capitalists) are also educated there and it’s a closed network. And he felt like my story of coming from a tier 2 town and as someone who has gone through a difficult childhood would actually resonate with a lot of people who are in normal jobs, and inspire them to believe that “hey, (if) this guy can do it, I can do it too.” And I thought that’s a very good point.

It's not a roadmap to success for a start-up, then?

It's not a business book; I was very clear about that. In fact, we attempted writing a Freshworks book before the IPO and we almost completed it, but we felt like, “Hey, it looks like a book on a different business model building from India, inbound sales and multiple products.” It was... not a ‘Girish’s story’ book. I didn’t want to write a business book and give gyan. I like giving anecdotes and letting people figure out their own lessons.

So, what are some of the basics that you find yourself going back to, since you mentioned that this book is more about inspiring others and identifying those ideas one can use as a springboard in life?

There are some life lessons which I constantly use. From a business standpoint, the biggest lesson that I have used successfully is riding the wave. During the dot-com era, I rode the Java wave. After the dot-com bust, I learned the importance of having a wave – even if you’re better (at what you do by the time the wave recedes), it doesn’t matter. You need the wave to create the tailwind. I think I did that successfully with Freshworks, when there was both a SaaS wave and social media wave. Now I would say AI is another wave that needs to be ridden. So that's the lesson: you must understand what’s currently happening, you have to be relevant for the next 5-10 years. That’s how a start-up can succeed. Riding the wave (is a life lesson that) has served me well.

Some of the life lessons, I think, will also help readers. In one of the earlier chapters, I talk about how I decided not to give the remote control of my happiness to anyone else. That’s a very powerful life lesson for me and it’s really helped shape who I am as well as contributed to my overall happiness in life – even before Freshworks.

What comes through also in ‘All In’ is this idea that you were constantly trying to upgrade to something better in life, and not just in terms of what class you flew in an airplane, or how you could get slightly better accommodation, or get an operation instead of living on pain medication, even though the operation cost a fair bit at that time...

I’ve always been aspirational. I believe that you can be aspirational and humble at the same time. And that’s the advice I give to my sons and some of the startup founders, because sometimes people confuse being aspirational with being aggressive.

I think I’ve always been aspirational, whether I had the money or not. And, probably, sometimes foolish enough to go after what I wanted without thinking about saving for the long-term. Because for me, I have to live in the moment and make sure that I can make the best possible use of it or the best possible option available. That has also become a life lesson for me; I like to optimize for happiness, not optimize for money. Sometimes it’s a material benefit that gives you happiness. Sometimes it’s the choice of your career. Sometimes it’s choosing where you want to live, or the people you want to associate with. But when I don’t give the remote control of my happiness to anyone else, that actually is part of that.

You talked about riding the wave a little earlier. You also talked about looking at AI in the SaaS space at a recent event in Chennai. Is artificial intelligence a wave that you’re looking to ride? If yes, how?

SaaS was a great opportunity for India. I would say it was the first catalyst in our dream of India as a product nation. And you saw companies like Freshworks or Chargebee or a lot of start-ups like BrowserStack emerge from that and growing successfully. AI is actually a booster which will offer even more opportunity for Indian startups to ride down this global opportunity. I think all SaaS founders should adapt.

There is no pureplay SaaS anymore. All SaaS products have to evolve as AI plus SaaS. You have to automate with AI and then bring a human in the loop to focus on higher order tasks.

That’s what I clarified in that SaaSBoomi event (SaaSBoomi is now BoomiAI) in Chennai – SaaS in its current form is definitely dead. We have to adapt to incorporating AI, really bring in the automation that businesses want and then deliver the value to further the business outcomes.

The AI that you’re talking about here is the low-lying fruit – what is already available, for example, customer service bots, etcetera – or are you also looking at deep-tech and integration within the services?

At the surface level, everybody can get AI to write an email or summarize a text or rephrase it and so on. All those are an API call to an underlying LLM (large language model). And customer service agent - the fancy term for bot today is an AI agent - if you are writing AI for customer service, that’s still not very simple actually. You can do a simple bot where you can feed in some knowledge and then ask questions and get answers. But let’s say you are doing customer service for a credit card company. Say someone calls the credit card company to know about a lost transaction or they want to make a payment or dispute a charge done on the card, those (tasks) require more integrations into the back-end system. I'm just using credit card as an example. (Similarly, for) hotel reservations, modifying a booking, cancelling a booking, changing the name of a passenger – these are tasks that are being done by humans today. AI agents today can not just answer questions from a pre-established knowledge base, but understand the context of the question, try giving an answer, but if it’s related to a specific transaction, actually interact with the back-end software, make the change and go back to the customer with a notification that their issue has been addressed. That is possible today. But we’d have to think about it from an industry-by-industry cycle, and that is just in customer service.

Now if you take industries like, say, US healthcare – most of the hospital chains still do manual medical coding and revenue cycle management where somebody has to collect all the data, feed in the codes, submit it to insurance so that the insurance company looks at it and then pays the hospital. I think that entire cycle of humans, at BPOs in India or Philippines, which does medical transcription, medical coding and revenue cycle management, that entire cycle is getting disrupted with a lot more automation.

A lot of traditional services industries like ad agencies, digital marketing agencies which used to offer digital marketing services to small and medium businesses that don’t have in-house teams to do things like, say, social media ads or Google Adwords, that entire agency model is getting fully automated with AI.

So, a lot more AI automation to replace traditional services-based or human-based work is actually possible today.

Are you also looking to train your own LLM for a specific vertical? Given the amount of compute required to do a general LLM, globally some firms seem to be looking at LLM for specific areas. Are you also looking to develop something that is a core Freshdesk product in AI?

We are investing in understanding our customer data more, building industry specific stuff as it is needed. I also have another vantage point as an investor, from Together Fund, where we are looking at domain-specific LLMs or more regional LLMs being built. And even across the AI stack, there are companies that are working on automatically providing the right data set, like multilingual data set. I was talking to a start-up a few days ago which had a lot of quality multilingual audio data, which actually is in scarce supply right now. So if Google Gemini or OpenAI wants to train their LLM on let’s say Bengali conversations, there’s not a lot of Bengali conversational data available online. So, I think there are startups that are trying to build voice models or provide the data for those voice models. We are seeing activity across all these sectors, yes.

Do you have a point of view then on whether Indian startups are focusing too much on delivering food instead of doing some of this deep technology work?

My point of view is #1, delivering food or doing payments online, there is a lot of tech that our companies have built in terms of fintech where India is far ahead. When I look at my life in the US versus my life in Chennai, here in Chennai, we are spoiled with Zepto and Blinkit and Swiggy, whereas there (in the US), you still have to order something and wait for it to come the next day. We can get something delivered in 10 minutes here. So, there is a lot of pioneering work that is happening. I'm not complaining about that.

But the deeper thought processes, see, it takes time to actually innovate. I run a grassroots football academy, right? Every four years, when the FIFA World Cup happens, a lot of people post on their social media: Why is India not in the World Cup now? It's a great thing to ask. But you have to think about it. For India to qualify in the FIFA World Cup, you have to first be in the top 5 in Asia and India is nowhere near the top 5 in Asia. So how do you get there? It takes time. It’s not like you wake up and decide to play in the World Cup.

If you look at even my own journey in 2010, no VC was looking to invest in B2B (business-to-business) startups. Everybody was focused on consumer startups. VCs would not travel to Chennai to meet a startup, right? That was the reality. And in 2015, when I was looking to plug into an ecosystem, there was no system available in Chennai. So we ended up creating SaaSBoomi. Today (in 2025), 70 investors flew in from different parts of the world. Many flew in from the US. Partners from marquee venture capital firms landed in India in 2025 in Chennai to attend SaaSBoomi, because they believe that a lot of action in AI is going to happen in India.

You have to be patient. My dream when we started SaaSBoomi was: We want to see India as a product nation. Look at it in snapshots of time; between 2015 and 2025, there's tremendous progress in terms of the number of startups. We were 40 startups building global products in 2016. There were 6,500 SaaS and AI startups in India in the SaaSBoomi database as of this year. (From) tier 2, tier 3 cities. There were 100 people from Gujarat attending SaaSBoomi in Chennai. There is a groundswell happening at the grassroots level in different cities.

So my answer to your question is, AI provides the opportunity for India to build and we need support from all factions involved: Investors should invest in deep tech, the government should provide infrastructure. With what's happening in the world, I think that will also happen. Maybe everybody understands that, ‘hey, you can’t rely on global trade anymore…’ Global trade is going through turmoil right now. So every country will look at making investments in their own infrastructure. So I think that will happen. We have to be patient.

Is there a big opportunity for India to win in AI? Answer is an absolute yes.

Globally, experts are comparing AI to the arms race. In this context, perhaps it won't be possible to be patient when it comes to AI? Because everybody is trying to get their products, their name out first. First-mover advantage is probably the reason why ChatGPT comes to almost everybody’s mind when you talk about generative AI. Is that something that you are concerned about, that maybe playing the long game is fine, but maybe you need to get there a little bit faster?

See, first of all, was ChatGPT built in a year? They, perhaps, have been working on this problem… this is the Roger Bannister equivalent, right? Nobody had run a mile in 4 minutes (before him) and then when somebody runs it, everybody else runs faster and the record is getting broken. So Open AI has been working on this problem for so long and finally they hit the breakthrough. And once people get that… it’s actually later you see Llama and Grok and Anthropic and everybody else doing it and DeepSeek did it even cheaper and better. I think that is not new, right?

Like when Freshworks was launched as Freshdesk, even then, the same argument could have been made that ‘Hey, three companies have come. So other companies cannot come right now.’ Facebook was not the first social media network. Before Facebook, there were many. Gmail was not the first email. Amazon was not the first e-commerce store. We had Rediff in India before Flipkart. So there will always be opportunity to offer something completely new, there will always be opportunity, if the category exists, for somebody to come and do something innovative and disruptive and do it much better than anybody else.

Speaking of protectionist tendencies, are you concerned about moves like the US tariff announcements earlier this year and tightening of immigration rules?

I think everybody should be concerned about US tariffs, because it’s not status quo anymore.

Global trade was a good thing. Many countries have benefited, including the US. I think a trade war will create a lot of tension. It's not good for anybody, to the extent that… if countries start retaliating, it is going to cause more turmoil. I think we all should be concerned and hope something will settle down and things can move forward.

On migration, I think, the action is mainly against illegal immigrants, which I think none of us can question. It’s a country’s sovereign right to protect it. So I’m not concerned about immigration.

When you say trade wars, are you referring to US versus China or is it US versus the world, including India?

In general, tariffs is one country against another. Obviously, it’s US and China (but it’s also the rest of the world). But the countries are now at the negotiating table and I think India is probably on the more friendly list with the US. So we'll get to the negotiating table first hopefully, and we will make sure we are better off.

You said that the book is not prescriptive. But given the kinds of decisions that you have made in your career and your work life so far, do you have any sort of tips for people who are just starting out in their careers? Perhaps, on how to pick something that is possibly going to be fruitful for them in the long run, and at a time when everything is just so much that is in flux? What advice do you give to your sons, for example, around this?

One piece of advice that I will probably give is… See, I am a chess player. Many times, there is an obvious move and it may be right most of the time. But there are a lot of times when the obvious move is not the right move. So you have to think deeper and find a better move. That is something which everybody can learn as a life lesson: the obvious move may not always be the right move. For example, if youngsters are joining BSc computer science today, it’s like an obvious move for many parents. Now, with AI disruption happening, I’m not sure if that could be the right move in terms of a career. By the time the child graduates after four years, how is the world going to be different? Is BSc computer science still going to be very relevant then? Or is the software developer job going to be the same as it is today? I don't know the answer to that, but I'm just using it as an example. Please don’t publish the title saying Girish Mathrubootham says software developers don’t have a future. I have 5,000 employees at Freshworks. I don’t want to cause any panic. But the point, the lesson is that the obvious move may not be the right move. That is one.

A lot of times we talk about trusting your gut. In the early stages of your career or life, when you don’t have enough experience, a gut-based decision, following your heart (may not always be advisable). Like when my friends warned me not to come back to India and start a startup after the dot-com bust, I simply wouldn’t listen because I really want to do it.

But a gut-based decision also is something where hundreds of invisible dots connect in your mind. As a startup founder, you know so much about your business or about your customers or about your market that you actually hold a deep conviction that this is the right thing to do. And people outside, when you go and ask them for advice, whether it’s investors or mentors, people who don’t have that level of understanding, they may give you different advice. So I think those invisible dots connecting in your mind is what I call a gut-based decision, where you feel like, ‘Hey, this is the right thing to do.’

Another example could be, you’re interviewing a candidate, and on paper, they are perfect. They have a great resume, great experience from a big company and so on. But in conversation, you don’t feel like the chemistry is right. Something feels odd, and you don’t seem like this person will be successful in the company. So then you go with the gut and say no, I’m not going to hire this person. I know this for a fact that every time I have ignored my gut and hired a person, it’s ended up badly. Now, I may not be able to articulate to the HR recruiter or the manager, at the time of interview, why I’m not hiring this person. But during the interview process, as a founder, you can feel whether that person will be a culture fit or not.

My advice to founders would be, respect your gut a lot more because of those invisible dots. Just don’t listen to outsiders giving advice all the time.

In the book you've mentioned that you would read these articles in business papers that asked CEOs about some of their personal preferences in luxury goods, and other things. Your love of cars and watches is known. But before we get to your favourites in those categories, tell us what a typical day in the life of Girish Mathrubootham looks like right now.

The good news is, there is no typical day because now I probably have a two-city lifestyle or sometimes a three-city lifestyle. My days in the US are very different from my days in Chennai or Bangalore.

In the US, my mornings start with meetings at 7.30 am onwards - my preferred start time - and I do a bunch of calls. I take a time-out between 3-7 pm - two or three hours during that time, I go and play tennis. Then I will have other calls in the evening. And then weekends usually are with friends, either watching movies or just catching up with them.

I'm also in the process of moving to the Bay Area.

Now in Chennai, my day typically starts off with waking up at 5.20. I've described that in the book also; I go and play tennis from 6-7.30 or 8 am. Then I come back, get ready and the meetings start from 9-9.30-10, depending on the schedule. And then again in the evenings, I will have US meetings. On weekends, I try and catch-up with my friends at home.

There are a lot of books behind you. Are you a big reader?

No, I think it makes for a nice display, background picture. I used to read a lot, especially during my school and college days. Generally, I don't read a lot of self-help or motivational books or anything like that. I like reading business books, as in stories. My favourite ones are ‘Shoe Dog’ (by Nike founder Phil Knight), ‘The Ride of a Lifetime’ by Walt Disney CEO Bob Iger. I buy a lot of books. I go through them. It's up to the book to then hook me in, and if I lose interest I just put it down. Sometimes I come back to it, sometimes not.

In ‘All In’, you mention Jack Welch’s book having an impact on you. Do you still look at Jack Welch as somebody that should inspire managers?

Jack Welch’s principles on hiring and firing are not lessons I would take from him. One thing I liked – it came from the book ‘Every Business is a Growth Business’ by Ram Charan – how can you go to your same customers and give them more products, or how can you take the same features that you have built and go to more customers. That lesson is from GE, but that (takeaway) was from the book by Ram Charan

In the book you've talked about your fitness routine, playing tennis and eating papayas now compared with mangoes from your courtyard as a child. Tell us a bit about your fitness regime, and how do you fit it into your day?

COVID in that sense was transformative for me. I hated being on phone calls all day. I started walking, and thankfully I was in California… (where) we were allowed to go out and walk. I used to walk like 10 kilometers every day and I started liking it. That's when I would either listen to a book on Audible or whatever. That walking and combined with a good diet program helped me lose a lot of weight. I went from 96 Kgs to 81-82 Kgs in the span of three months. And that felt really good. I felt energized. But when you lose so much weight, suddenly your friends start telling you that, ‘Hey, you look sick.’ So I thought, ‘OK, I'll start working out’, and I had time. When you're not travelling all around the world, you have a lot of time suddenly. We got a trainer to come home and started working out and I really got into better shape and realized how impactful this is and how abusive we have been on our bodies for so long with all the food habits that we have. I think the most important lesson that I learnt (with respect to health) is fitness is all mostly about food, right? So, you have to eat healthy and you have to cut down the amount of carbs. Just reducing the quantity of fuel intake or food intake and combining it with activity like tennis has allowed me to really find balance.