“Entrepreneurs Are Problem Solvers”: Ashish on Building Businesses, Choosing Careers and India's AI Future

In this conversation with students at an entrepreneurial university, Ashish Kashyap reflects on the experiences that have shaped his approach to business, from his time at Google to building ventures such as Goibibo and INDmoney. He discusses how entrepreneurs identify meaningful problems, why early career professionals should seek opportunities to work close to innovation, how artificial intelligence could transform businesses, and why resilience is essential to building a company.

Pratham Mittal, Founder of Masters’ Union, interviewed Ashish on his YouTube channel. We are publishing an edited version of this conversation for our readers.

Finding Energy in Solving Problems

Interviewer: You have built several well known businesses, including Goibibo and INDmoney, and have also been involved in building a university. These are substantial undertakings. Where do you get the energy? Are you ever satisfied, or are you always looking to build something new?

Ashish: For me, it comes down to solving problems. I think most entrepreneurs enjoy solving problems. I do not want to generalise, but people like us find satisfaction in identifying a problem and working towards a solution.

Take the financial services space, for example. Many of us use products and services from companies such as Google, Facebook and Apple every day. Yet, while we can use these companies' products, we may not have an easy way to invest in them.

If I can invest in a company such as Hindustan Unilever, why should I not be able to invest in Google, Facebook and other companies whose products I use regularly?

I wanted to create that opportunity for myself and others. The idea was to make these companies accessible through fractional investing and to make the process of moving money easier as well.

When you identify a problem that matters to you and become invested in solving it, the work itself becomes motivating. That is what keeps me going.

How to Choose the Right Business Idea

Interviewer: How do you decide which business to start? Do you follow a particular playbook or mental model? Do you begin with the problem itself?

Ashish: Yes, I begin with the problem. I should be able to relate to it personally. There is a saying that only the person wearing the shoe knows where it pinches. I think there is a lot of truth in that.

If I cannot relate to a problem, it becomes difficult for me to understand it deeply. But when I have experienced it myself, or can clearly understand why it matters, I am more motivated to solve it.

There is a little bit of selfishness in this process. I ask myself whether solving the problem would benefit me. If the answer is yes, I then ask whether it would benefit other people and whether they would derive meaningful value from the solution.

That becomes the hypothesis.

The next question is the scale of the opportunity. Could the solution make a difference to millions of people? Is the market large enough? These are important considerations.

However, the starting point is a personal connection with the problem. Once you have that connection, you need to examine whether the problem is widespread and whether existing solutions are addressing it effectively.

Sometimes, when you ask people about a problem, they will tell you that several companies or institutions are already working on it. But the existence of solutions does not necessarily mean that the problem has been solved well.

You have to look beyond the number of companies in the market and ask whether customers are genuinely getting the outcome they need.

That is an important way to evaluate a business opportunity.

From Goibibo to a Broader Business Group

Interviewer: Your professional journey includes Goibibo, the broader Ibibo Group and PayU. Could you explain how one startup evolved into multiple businesses? What was the strategic thinking behind that journey?

Ashish: The story began with Goibibo, the online travel agency. When we were building the business, we encountered a significant problem with payment failures.

At that time, we were using a payment gateway called CC Avenue. Payments would fail frequently, and the success rate at checkout was only around 60 per cent. That was a serious problem.

Consider the customer experience. A person searches for a flight, selects a ticket and proceeds to payment. If the transaction fails, the customer has to try again. Sometimes the customer may have to repeat the process several times.

This creates frustration and can also result in lost business.

I began examining why these failures were happening. Payment gateways connect merchants with multiple banks and coordinate transactions through technical integrations. At that time, the technology was still relatively immature, and those connections could fail.

We realised that improving payment success rates could make a substantial difference to the business. If we could increase the rate from 60 per cent to 80 per cent, the improvement would have a significant impact on our economics and customer acquisition.

So we decided to build our own payment system.

We established banking relationships and maintained fixed deposits with different banks as part of the arrangement. By building this system, we did not merely improve the payment success rate to 80 per cent. We were able to take it to approximately 85 per cent.

That was a game changer for us.

Once we had solved the problem for our own business, we asked a logical question: why not offer the same capability to other merchants?

That was how the payments business developed. What began as an internal solution to a problem in the travel business created an opportunity to serve other businesses as well.

The broader lesson is that solving one problem can reveal another business opportunity. Sometimes, a capability you build for yourself can become valuable to an entirely different set of customers.

Choosing a Career After Graduation

Interviewer: Many students here want to become entrepreneurs. At the same time, they face pressure to secure jobs after completing their degrees. You worked at Google before moving into entrepreneurship. What advice would you give young professionals who are trying to decide between joining a large company and working with a startup?

Ashish: Let me be honest. My experience at Google was quite depressing in one particular sense, although I learned a great deal there.

I was working during a period when the level of innovation happening in Silicon Valley was striking. People were constantly discussing problems, developing ideas and starting companies. There was an energy around building new things.

In India, at that time, many graduates were primarily thinking about joining established technology companies or software services firms. Far fewer were thinking about building products and creating new businesses.

The contrast was frustrating. I could see the innovation happening in the United States, and I wondered why we were not seeing the same level of activity in India.

Of course, India's technology ecosystem eventually developed considerably. Internet access became more widespread, connectivity costs fell and a new generation of companies emerged. But that transformation took time, and many businesses were created and many others disappeared along the way.

One important lesson I took from that experience was the importance of working close to the core of a business.

In a large multinational company, a significant amount of work may involve distributing, marketing, selling or maintaining a product that is being developed elsewhere. The central innovation may be happening in another country or another part of the organisation.

The company name on your résumé may be impressive, but that alone does not guarantee that you will learn how to build a product or solve a fundamental problem.

If you want to learn how businesses are created, you should try to work where the core product, technology or business model is being developed.

Interviewer: That is an important point, but what about someone who has just graduated? They may not have enough experience to join a company in a core role.

Ashish: I do not think it is simply a question of years of experience anymore.

I have seen people with three years of experience create considerably more impact than people with twenty years of experience. That does not mean experience has no value. People are at different stages of their careers, and their circumstances differ.

But the number of years someone has worked is not necessarily a reliable measure of how much value they can create.

My advice to students is to avoid choosing a large multinational company simply because it is a large multinational company. There are exceptions, particularly if you are working on the company's core artificial intelligence systems, language models or other important technologies. But if you are far removed from the core, your learning may be limited.

Instead, look for companies that are solving important problems and give yourself the opportunity to participate directly in that work.

A product manager or engineer working in such an environment may have a demanding schedule. Work life balance can be a challenge. But people who have worked with me over the years often tell me that their learning has been many times greater than what they expected.

When you learn faster, you can experiment faster. When you experiment faster, you can create impact sooner. And when you eventually decide to start your own company, that experience can improve your chances of success.

The key is to work close to the people who are building the core of the business, whether the problem is global or specific to India.

India's Position in the Global Technology Race

Interviewer: There is a great deal happening in Silicon Valley, from artificial intelligence and genetic engineering to brain computer interfaces. Sometimes it feels as though India is always behind. How do you see the future? Will India remain ten, twenty or thirty years behind the leading technology centres?

Ashish: First, we need to be honest with ourselves.

There are core technologies that India has not built at the level we would like. Take semiconductor chips, for example. We depend on other countries for important parts of the semiconductor ecosystem, whether manufacturing or advanced design.

We should acknowledge these realities rather than pretending that we have already achieved everything.

There is a tendency to complain about why India missed a particular opportunity or to blame the government. But every country, company and startup evolves in its own way. We need to understand where we stand before deciding what to do next.

For example, if we missed an important wave in the development of large language models, we should recognise that. We may or may not catch up in every part of the GPU ecosystem. We need to be realistic about that as well.

But recognising a gap does not mean giving up.

The more productive question is how quickly we can adopt these technologies to solve problems that have been difficult to address until now.

Artificial intelligence can help us solve problems faster, more effectively and at a lower cost. We should think about how to use these capabilities aggressively.

Consider financial advice and family office services. Historically, sophisticated financial advice and wealth management have largely been available to affluent customers. Could AI make some of these services accessible to a much wider population?

That is the kind of opportunity we should be exploring.

Rather than focusing only on the technologies we have missed, we should identify the problems we want to solve and work out how emerging technologies can help us solve them.

Which Industries Should Entrepreneurs Explore in the AI Era?

Interviewer: If someone wants to start a company today, which industries or business ideas should they consider? What would you look at first?

Ashish: I would begin by thinking about the customers and the problems they face.

Broadly, I think about two types of customers. The first is the individual consumer. The second is the institutional customer, which could include businesses, government organisations and other institutions.

Both have fundamental problems that need to be solved.

During the evolution of the internet and mobile technology, many consumer businesses were built around websites and graphical user interfaces. Customers opened an app, navigated through screens and completed tasks themselves.

I think we need to rethink that model.

In the future, some of these journeys may be disrupted by artificial intelligence agents, data pipelines and systems that can take action on behalf of users. Instead of requiring people to spend hours navigating interfaces and completing repetitive tasks, we may be able to delegate much of that work to AI.

Consider filing income tax returns. It can be a laborious process, even for chartered accountants, particularly when a person's income and financial information do not fit neatly into standard formats.

Could an AI agent collect the relevant information, identify inconsistencies, perform the necessary checks and help complete the process more efficiently?

That is one example of the problems entrepreneurs could explore.

On the enterprise side, the opportunity is to make organisations more productive. How can AI automate time consuming processes? How can it help employees complete tasks faster? How can it reduce repetitive work and improve the quality of decisions?

These questions should influence how we design products.

We may need to rethink user journeys, workflows and interfaces. I do not think we should assume that today's mobile app interfaces will remain the dominant way people interact with technology.

The larger opportunity is to use AI to make products and services more useful, more accessible and easier to operate.

How INDmoney Is Adapting to AI

Interviewer: How are you preparing INDmoney for this future?

Ashish: We are working on it. Unlike some newer companies, we also have an existing business and a product history, so adapting is not always straightforward.

We have started embedding large language models into our product to enable more capabilities.

For example, our customer service is now driven by an AI chatbot. That is a relatively straightforward application, and many companies are doing something similar.

Beyond customer service, we are looking at ways to enable people to obtain financial advice and take actions through our platform.

The important thing is to move beyond using AI as a superficial feature. We need to examine how it can genuinely improve the experience and help customers accomplish what they want to do.

Handling Self Doubt as an Entrepreneur

Audience Member: You have built several successful ventures. Which startup gave you the hardest nights of self doubt? What were you questioning, and how did you overcome those moments?

Ashish: The entrepreneurial journey is extremely volatile. One day, you feel that everything is going well. The next day, you wonder whether you are making a huge mistake.

Even today, those feelings occur.

Every venture has days when you question what you are doing. You may wonder whether the strategy is right, whether the business is working or whether you should be focusing on something else.

Those are the days of self doubt. They can occur very frequently.

I think you need to be honest with yourself. You cannot build a business by refusing to acknowledge that something is wrong. You need to recognise problems and be willing to change your approach.

At the same time, you have to be resilient and thick skinned. When you are building something new, you will often encounter more people discouraging you than encouraging you.

It is easy for people to criticise. What matters is whether you can distinguish useful criticism from negativity and continue working on the problem.

One thing that energises me is hearing directly from customers. When someone says that they love the app, that it has solved a problem for them or that a particular feature has made their life easier, it gives you a reason to continue.

We also receive feedback through platforms such as Google Play and the iOS App Store. Not all of it is positive, but feedback helps us understand what customers are experiencing.

There are days when everything seems broken and nothing appears to be working. There are also days when you feel that you are making a real difference.

That fluctuation is part of entrepreneurship.

I would say that the current venture has been more challenging in some respects because we are dealing with a larger audience and a more complex regulatory environment. In financial services, competition and market timing are not the only considerations. Regulations also shape what you can and cannot do.

For example, we initially considered using influencers to educate people about our product. However, we encountered regulatory restrictions around the use of influencers in financial services and investment related activities.

That meant we had to rethink the approach.

You have to keep adapting. And, over time, you tend to forget some of the difficult periods you experienced in the past.

Building a Regulated Financial Services Business

Audience Member: I have two questions. First, what are your views on specialised investment funds, or SIFs, introduced by SEBI? Second, what direction is INDmoney moving towards? Do you see the company eventually obtaining licences to manufacture mutual funds or offer portfolio management services?

Ashish: Let me begin with the second question.

There are already many mutual fund manufacturers in the market. If I were to launch another mutual fund, I would first have to ask whether I was actually solving a problem.

I have not yet identified a sufficiently compelling reason to enter that business in the conventional way. There is also the regulatory complexity to consider.

That does not mean I am ruling out asset management entirely. I would be more interested in exploring specialised products designed for particular groups of investors.

Our thinking might also change as the business grows. We currently have approximately 2.5 million active investors on our app. If we had 25 million or 30 million investors, we might look at the opportunity differently. We could ask whether we should offer a particular investment solution directly to our existing customers.

However, we would also need to understand the regulatory implications. SEBI and the Reserve Bank of India have distinct regulatory responsibilities, and the separation between activities regulated by different authorities matters.

On licences, our experience has taught us not to depend on borrowed licences indefinitely. We want to be properly licensed and regulated for the activities we undertake.

We have obtained a licence through GIFT City for our US securities offering. That process required us to engage with the regulator and explain the structure of the business.

There were concerns about money moving out of India. We explained that the system was designed as a closed loop, with funds returning to the same account through which the customer had initiated the transaction. That helped clarify the model.

We also have domestic securities related licences and have obtained an RBI NBFC licence for lending against mutual funds and shares. Previously, we conducted such lending through banks and other intermediaries.

We have also been working on capabilities such as automated income tax filing.

The broader lesson is that financial services companies must take regulation seriously. Engage with regulators, understand the requirements and do things properly. Avoid operating in regulatory grey areas.

In this sector, it is important to be clear about what you are permitted to do and to build the business accordingly.

Is Good User Experience a Competitive Advantage?

Audience Member: I use your apps regularly, and one thing I have noticed is the emphasis on user experience. Do you see good design as a competitive advantage or as a basic requirement? And how will user experience change as AI agents begin to replace conventional mobile app journeys?

Ashish: As entrepreneurs, we all appreciate good design. But I do not think we should become excessively obsessed with design for its own sake.

We should use data to understand where both the customer and the company can achieve better outcomes.

For example, we need to examine conversion rates. How many people begin a process, and how many successfully complete it? Where do customers drop out? How do the results vary across different customer groups, use cases and platforms such as Android and iOS?

Those findings should inform design decisions.

Design should help the customer accomplish something and help the business deliver better outcomes. It should not become an end in itself.

As AI changes the way people interact with products, our metrics will also change. We may need to understand what commands customers give, how effectively the system interprets those commands and how often it completes the intended task successfully.

The measures of success will evolve with technology.

However, certain principles will remain important. Low latency, simplicity and reliability all matter because customers want things to work quickly and easily.

Ultimately, design should be guided by the outcomes we want to create.

How Do You Know Whether a Market Is Large Enough?

Audience Member: You mentioned that entrepreneurs should look for problems worth solving. How do you determine whether a particular market is large enough to justify building a business around it?

Ashish: I would look at two possibilities.

The first is that a large market already exists. The second is that a market could emerge if someone solves a problem in a new way.

Before companies such as Uber and Airbnb emerged, the markets they created did not necessarily exist in the same form. Their businesses changed how people accessed services and created new ways for supply and demand to come together.

In such cases, you need to look for a substitution effect. Is there an existing activity, expense or behaviour that your product could replace or improve? That can provide an indication of the potential market.

In our case, we looked at the number of people who invest and the extent to which people participate in capital markets.

If only a small percentage of the population participates in these markets, that may indicate a significant opportunity to make investing more accessible.

You need to understand how large the existing market is, how it might grow and what proportion of it your solution could realistically serve.

The important thing is not to rely on a large market estimate alone. You must understand the underlying customer behaviour and why people would adopt your solution.

Should Every Entrepreneur Aim to Build a Large Company?

Interviewer: Let me approach the question differently. Do entrepreneurs always need to aim for a large, scalable business? Could someone start a small pizza restaurant or coffee shop instead? Students often feel conflicted about whether they should pursue a big idea or build something smaller.

Ashish: There are different approaches, and both can be valid.

Let me give you an example of a company that serves a relatively small number of customers. It has approximately 500 customers, yet it has built a business valued at around billion, according to the example I was discussing.

A substantial proportion of its revenue comes from its largest customers. It demonstrates that you do not necessarily need millions of customers to build a valuable business.

You can build a large institutional business by serving a relatively small number of customers if the problem is important and the value you provide is significant.

On the other hand, suppose you want to build a boutique coffee shop. You want it to be the best coffee shop in a particular business district, a place where people have excellent conversations, enjoy good music and return because they appreciate the experience.

You may want to open one shop, make it successful, earn a good living and eventually open another.

That is also a legitimate ambition.

The two approaches are different. In the first, you may be trying to build a large organisation that serves a major market. In the second, you may be trying to build a business around your interests, your lifestyle and the customers you want to serve.

There is nothing inherently wrong with either choice.

The difficulty arises when people are unclear about what they really want. They may say they want to build a large organisation but pursue a business model that does not support that ambition. Alternatively, they may want a comfortable, independent business but feel pressured to pursue a high growth startup.

You need to be honest about your ambitions and choose accordingly.

There are also paths between the two. You could start with a small business, learn from the experience and later build something much larger. You could work at an established startup, develop your skills and then launch your own venture.

There is no single right or wrong route. What matters is that you understand what you want to build and why.

Closing Thoughts for Aspiring Entrepreneurs

Interviewer: Do you have any questions for us before we conclude?

Ashish: I think you are a very energised group of people. Thank you for having me here. I know everyone has a busy schedule, and I appreciate the opportunity to spend time with you.

It has been a pleasure meeting you all. I wish everyone the very best for the future.

Interviewer: Thank you for joining us and sharing your experiences. We appreciate your time and the insights you have offered our students.

Editorial note: This version has been edited for readability and publication. Some passages in the original automatic transcript were unclear, so I have prioritised preserving the speaker's apparent meaning rather than presenting every sentence as a verbatim quotation. The company's valuation, investor numbers, licensing references and other time sensitive statements should be verified against the original recording before publication.

Courtesy: https://www.youtube.com/watch?v=aYqgXabUWWs