While Dubey pursued his startup dreams, Singh financed their life by taking up a well-paying job in the government, supporting not just Dubey, but his two co-founders too—transforming their 2-bedroom apartment in Mumbai into a startup hub in 2005.
From writing the first cheque for CarWale, Dubey’s first startup, to taking on a leadership role in the company, Singh also got a taste of the entrepreneur’s life. Later, Singh even launched her own venture, Rangreza, blending her passion for fashion and social impact.
In 2019, she joined Dubey again in the quest for building a bus technology platform Chalo, after he sold his first company. With her experience working in the public sector and building a company on her own, Singh today is driving the company’s vertical in the government mobility space.
Chalo, which raised $119 million in funding so far from marquee investors Avataar Ventures, Lightrock India and WaterBridge Ventures, among others, was last valued at $400-450 million. It provides services including live bus tracking, digital tickets and passes, live passenger indicator, fleet management, and contactless payment solutions.
Present in about 66 cities in India, Chalo is now focusing on overseas expansion and is already operating in the Philippines, Peru, Bangkok and Fiji, Singh, co-founder and director of Chalo, said on Mint’s Founder Diaries series.
Singh shares her journey – from cutting the first cheque for her husband Dubey’s startup to branching out on her own, and eventually building Chalo alongside Dubey and their co-founder Dhruv Chopra.
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You’re from a small town near Bhopal. Did you ever think about starting your own venture when you were young?
I never thought of starting anything when I was growing up, but I’m the kind of person who takes a lot of initiative, takes risks, and experiments. I like to try things and see if they work. Even if someone says no to me, it’s in my nature to believe that things can still happen. If someone tells me something won’t work, I’ll keep pushing because I feel it can.
Whenever Mohit proposes something, I just say, ‘Let’s do it, let’s try.’ I don’t think about whether it will fail; I usually think it will work.
You have a strong focus on social impact and have been involved in various social initiatives. Can you share more about that?
I did a master’s degree in social work, but even before that, during my childhood, I became interested in doing work that impacts human lives. I continued doing it—working in hospitals, assisting with traffic management, and even managing traffic at a central station in Vidisha, the city I’m from.
Even if someone says no to me, it’s in my nature to believe that things can still happen.
I’ve also worked with communities affected by HIV/AIDS as well as women infected with RTIs (reproductive tract infection) and STIs (sexually transmitted infection). I worked with leprosy patients too… Both my parents were very supportive.
Your entrepreneurial journey really began after meeting Mohit. Could you tell us more about that?
So, I got married very early—right after I graduated from college. One day, Mohit said he wanted to leave his job and do something else. I said, ‘Yeah, do it.’ He couldn’t believe it and asked, ‘Are you sure?’ because we had been married for only two months.
At that time, he was the one earning, and I was in social work, which, as you can imagine, doesn’t pay much, especially if you’re interning with an NGO. We were living in Mumbai, but I told him, ‘No, you should do it, and I’ll figure out how to manage the finances.’
What was it like living with three co-founders? I’m sure there were plenty of late nights filled with brainstorming and ideation. How did you manage that?
He kept figuring things out, and I kept supporting his ideas. For seven years, he was working on ideas and during that time, I was financing not only his work but also supporting his two co-founders who lived with us. I was financing everything. I paid for their food, sponsored their journeys and covered all their expenses.
Fortunately, I was doing well in my job, and I had established a good career, so I was able to fund their startup, which was actually being run out of our two-bedroom apartment.
I was very clear that I wanted to be with my family. Being together was a priority for me, so I decided to leave my job and move to Mumbai with him.
The group was great, and Mohit was very modern in his thinking. He would show me presentations and I’d give my inputs. Sometimes, I would even go with him to business meetings while still doing my job. If I didn’t have an entrepreneurial mindset or a willingness to take risks, I wouldn’t have been able to tolerate this for seven years.
One month it was telemedicine, the next it was something else. This went on for about seven years. We got married in 2005 and I remember it wasn’t until 2019 that things really started to take shape.
Finally, in 2006, he came up with the idea to create a model for buying and selling cars (CarWale), where people were struggling to navigate the process. That’s when he got his first cheque.
How did you decide to join Mohit in his entrepreneurial journey?
I was a shareholder in CarWale because I had cut the first cheque for them of about ₹50,000. We moved to Mumbai when Mohit received his first external cheque because his investor said he needed to be in Mumbai.
At that time, I had a state-level job with the government of India, and it was a highly prestigious opportunity. But I was very clear that I wanted to be with my family. Being together was a priority for me, so I decided to leave my job and move to Mumbai with him.
If I didn’t have an entrepreneurial mindset or a willingness to take risks, I wouldn’t have been able to tolerate this for seven years.
That’s when Mohit suggested I join CarWale. I asked, ‘What will I do?’ He said he wanted to build a cohesive culture and that I should lead the culture and people aspect. I was offended. I never considered HR as an option for me.
It wasn’t something I could decide in 15 or 20 days, so I worked pro bono for 5-6 months. It was a big commitment to work with him and I needed to check the team chemistry. They had a very close-knit group.
Eventually, there was pressure on me to formally join the company because things had been going on for a while. I joined as the AVP for people and culture and that’s how it happened.
Tell us about your solo venture Rangreza?
In 2017, I went to Stanford for a short course because I felt I wasn’t very good with strategy and finances. So, I sold my shares and got some money. After that, I decided to enhance my skills through studies.
I was working on a project called Rangreza, inspired by my love for clothing. I often buy new clothes but wear them only a couple of times before they sit in my wardrobe.
My reason for wanting to leave was different. I felt it was essential to work with a diverse team and different people to gain new perspectives and ideas.
I thought, why not sell them at a 60-70% discount and raise money to give back to society? That’s how the model came about. Mohit encouraged me to try it, so I started working on it.
Ultimately, I got selected for the Stanford programme and I was also running Rangreza at that time. My entire design-thinking project was part of the course I did at Stanford, and it has since become a part of their curriculum.
If you take the same course now, you’ll encounter the Rangreza case study. It’s one of my biggest achievements, and I feel incredibly blessed.
You mentioned there was some apprehension when you were considering joining Chalo with the same team. Can you elaborate why?
When you work with people for seven or eight years and live with them all the time, it creates a strong bond. My reason for wanting to leave was different. I felt it was essential to work with a diverse team and different people to gain new perspectives and ideas.
I started Rangreza to explore this. However, I had also invested in Chalo and was a shareholder, so I remained connected to the team.
In September 2018, one of the board members approached me and said I should come back. I initially resisted, insisting I wouldn’t join the same team again.
The misconception that women can balance everything leads to problems.
Later, he made me realise that my strengths could contribute significantly to the team and that together we could create a more substantial impact than we could individually. So, I decided to join. I started working on April 12, 2019, in human resources, but I often told Mohit that I wanted to do more than just that.
In 2020, when Lightrock came on board, they looked at my profile and noted its diversity. One of the female chairpersons, Vaidhehi (Ravindran), asked Mohit why I was sitting in HR with such a varied background in public sector, government, private, and startup experiences.
She suggested I should be doing more business-related work. Mohit was excited about this and encouraged me to attend a few upcoming meetings. I took his advice and went to those meetings. It became very successful. I lead one of the largest markets for this company.
Did other companies earlier try to solve this problem?
There are some companies that are solving parts of the problem, but when it comes to live tracking, I believe we have gotten it right in a way that nobody else has so far.
Others are addressing specific issues: someone is focusing on ticketing, another on API transactions, and yet another on live tracking. We are solving everything with a comprehensive, full-stack approach.
I still believe that for a woman starting an organisation, her journey is significantly harder compared to a 26-year-old male entrepreneur.
Our model is a plug-and-play system, although some adaptations are necessary from city to city based on specific requirements. We also build dashboards for governments and operators to monitor key metrics such as ticket sales, digital transactions, and cash transactions. These dashboards provide real-time insights.
In Nagpur, for instance, we are managing the entire crew and field staff because the local government requested leak-free buses. This is just one example of our operational management.
When we look at international markets, we see similar models in places like the Philippines and Peru. There, we encounter even poorer services than in India, highlighting potential markets where we can create significant impact and improve lives.
Last year, you secured substantial funding, particularly aimed at this international growth. Could you share what progress has been made since then, and what your plans are?
We are currently operating in around 66 cities. Internationally, we are present in the Philippines, Peru, Bangkok, and Manila, and we are exploring one more country that we will announce soon.
Fiji is one country wherein we have signed up around a couple of operators.
You mentioned the challenges around funding for female co-founders. What are your thoughts on this issue?
Because I had male co-founders, and they have been successful. It became easier for me. I think if I were running this alone, it would be much tougher.
However, I still believe that for a woman starting an organisation, her journey is significantly harder compared to a 26-year-old male entrepreneur, even if the male might not perform well and still receive funding.
While men generally feel assured they’ll succeed, women sometimes question whether they will receive opportunities or support. Societal backing for men is often stronger, while women continue to grapple with household responsibilities, self-image issues, and guilt.
Men can’t have it all, either. The misconception that women can balance everything leads to problems. Many women who do that feel the pressure to perform in all areas.
