When Anisha Singh tells you, “You cannot align your chips,” she isn’t just spewing a cliché. Here is a woman who started out in life with a firm resolve of never running a business. For, as a youngster, she had seen her dad’s business struggle. So, when it was time to build her career, she chose the stability of a corporate job in the land of opportunities.

And yet, to the surprise and dismay of many, she not only moved back to India in a couple of years but also co-founded a company that had a very humble beginning. Today, this self-proclaimed “Queen of Averages” is every start-up’s role model, as her venture, Mydala, is valued at over Rs 1000 crore. This is her story of grit and gumption.

Having read a description of Anisha as “Hurricane Anisha”, who “zips through her days with enough energy to put Hurricane Sandy to shame”, on Mydala’s website, I thought I was suitably prepared for my meeting with her. And yet, nothing can really ready you for meeting this powerhouse of energy and confidence. The Okhla office of Mydala was both an ideal setting and a fitting prelude to this meeting.

For someone who grew up with a strong resolve of becoming anything but an entrepreneur, Anisha’s story is the stuff that dreams are made of. She co-founded Mydala, India’s largest coupon company, with Arjun Basu (her long-standing friend and now her husband) and Ashish Bhatnagar. The company is today the poster organisation of the dotcom space, having turned profitable at a time when many others are either continuing to burn cash or have shut shop.

“I was the queen of averages for the first part of my life,” she says, as we start to trace her childhood journey.

That sounds discordant in the current setting, with Mydala being any start-up’s dream. She continues to narrate how for the first fifteen to seventeen years of her life, she went about her ways without any goal. Two things she knew for sure though. The first, she didn’t want to become a dentist. Her mom was a dentist and her tryst with injections and blood left the daughter unimpressed. The second, she would never take to business.

With Mydala’s phenomenal success, “never say never” has become a standing joke in Anisha’s life. As you probe her on this decision, she has a tale that endears young Anisha to you instantly. Her father, who was an ex-serviceman and involved in a thriving business with his father, started a real estate business of his own following a family tiff. While they continued to live in their family home and everything seemed fine, financially they fell upon hard times, so much so that paying even the school fee turned into a monthly challenge.

She explains how she has this aversion to potatoes because that’s what she ate as a child for the longest time, being one of the cheapest vegetables available.

Back then, she knew for sure that as an adult, she was going to pick up a stable job with a steady paycheque and that entrepreneurship would not feature in her scheme of things.

The solemn tone of the discussion suddenly perks up as you get a glimpse of Anisha’s never-say-die attitude through an anecdote she narrates. A strong believer in the power of dreams, she recalls how even in that low phase, she never stopped dreaming. Every morning while on her way to the Air Force School, when her school bus passed by the sprawling houses on Palam Marg in New Delhi, she peered at them, confident that one day she would be a proud owner of one of them and not just a mere passer-by. This, at a time when owning just about any house was a luxury that they couldn’t afford. She tells me how she doesn’t let a single occasion go by when she does not tell her dad that the power of her dreams has today put him at his current Palam Marg address.

Not one to mince words, she admits that she was just an average student and even recalls how a professor during her undergraduate course held her up as a model for other students not to emulate, as he thought she wouldn’t go far. A prediction that couldn’t be further away from the truth!

Interning with the Discovery Channel after her undergraduate studies, she happened to meet someone who had studied political communication, and decided to follow suit. Accepted by the American University, USA became the setting for Anisha’s sojourn for the next few years. She recalls how even there she remained quite uninspired early on, until a chance encounter with a teacher-turned-mentor egged her on to utilize her full potential.

Armed with a new-found belief in herself, Anisha enrolled for an MBA programme. The high point came when she interned with the Olympus Group in the DC area led by a woman called Julie Holdren. “Julie walked on water,” says Anisha. A mother to twins, she ran a start-up of 400 people and did thirty push-ups a day; Anisha knew that she wanted to be like her some day!

She confesses that the seeds of entrepreneurship were possibly sown even earlier when as a student, she babysat for $14 an hour.

There’s pride on her face as she recalls how she did that to support herself. The real taste of entrepreneurship, however, came about during her stint at Capitol Hill where she worked with the Clinton administration for National Women’s Business Association. Merely twenty-one, she helped raise funds for innovative women-led businesses. She spent her weekends looking at thousands of business plans. The high point that made her look forward to her weekends, however, was that every plan came with a two-page note about a woman and her life. Anisha realised early that the world is “full of some phenomenal women”.

As for her own career, she was still steeped in the concept of job stability and started to work for a large software firm in Boston, where she helped set up e-learning ecosystems for Fortune 500 companies. It was during this time that she saw a big market for e-learning solutions which she felt she could tap on her own. This was also a time when although she was perfectly comfortable with her life in New York, returning to India was a tape that had slowly but surely started playing in her head.

While she had enough experience of the domain, given her corporate stint in the area, taking the plunge was indeed a big decision, more so for someone who had grown up counting the merits of a steady income. Setting up a company meant deploying her hard-earned savings and redeeming her stock options towards an unchartered territory. Her own demons made the journey even tougher.

Arguably, moving back to India was in itself a big decision and there were many cynics in the land of opportunity, who advised her against it.

She was not only changing career midstream, but also her whole way of life with a change in country. When asked how she traversed this part of the journey, she recalls how she returned to India with only one suitcase in order to test the waters.

Determined to leave nothing to chance, she particularly remembers meeting Deep Kalra of MakeMyTrip to get an industry perspective. Encouraged by his response, the one-suitcase visit to India turned into a permanent one. She recalls being so consumed by the idea and its execution that she could not even go back to the US to shift her stuff. It was her sister-in-law who did all the spadework for the relocation.

With an eye on the growing e-learning market, KINIS Software Solutions was launched in 2007, as a joint venture company with a US-based firm. What started as a homegrown company soon started to provide high-end e-learning solutions to companies in the US and the UK and also to the domestic market. When asked if the journey was hunky-dory all along, she is quick to recall a stage early on where she was “lying curled up on her couch” worried about the fact that she did not know how she would pay the next month’s salary to her employees.

Fortune as they say, favours the brave.

That very month, the company got a large project that not only care of the salaries but also put her comfortably on the road. “As an entrepreneur,’ she says her biggest learning has been that, ‘you cannot always align your chips. You could be the richest person and life could still change in a minute.”

With KINIS software in self-sustaining mode two years later and a junior partner running day-to-day operations, Anisha began to explore new horizons. Researching various business models online, she chanced upon a model in China where people got together physically, as a group, to avail of deals. Groupon at this time had only just come into existence in New York, though far from a full-blown deal site that it is today. The idea resonated with Anisha in the Indian context especially, as Indians’ love for a good deal is well known.

When asked if fear had any place, since this time she was treading on an unknown path, she tells you how “life literally happens”. While entrepreneurship wasn’t a part of her broad plan in the first place, when opportunities came around she “didn’t overthink”. There’s only one thing that she recommends, which is absolutely non-negotiable – “sufficient groundwork”. The one piece of advice that she has for wannabe entrepreneurs is to have a viable business plan and not just strive for a high valuation.

Beyond this, when considering entrepreneurship as an option, she says the only thing that helps is to think of the worst-case scenario.

“As long as you are sure of a roof over your head and food on your table, you cannot go too wrong.” A learning that clearly draws on her childhood experience. “After all, if you fail once, you can always start over again,” she says determinedly.

Mydala, she explains, had a very humble beginning; its first office shared space with her mother’s dental clinic. Soon after the company came into existence, Anisha also found out that she was carrying her first child. She is at her witty best in describing a spate of interviews where a pregnant woman sat next to a dental chair and explained to candidates the “big picture” of how Mydala is set to break new ground. If people bought in to her vision, it, of course, speaks of her sheer passion and belief but also, as she is quick to point out, “it takes some serious commitment” on the part of the candidates to come on board a new venture. On her part, she made sure that she recruited such committed people. Most of her core team, she proudly mentions, has stayed on to see the journey of Mydala, no mean feat in today’s scenario of growing attrition.

The pregnant entrepreneur went on to work into the wee hours of the morning every day, surviving on “daal naan in true start-up culture”, so much so that everyone started telling her that Daal Naan is what she should name her progeny.

She recalls how even on the night of her delivery, she was in the office till 1.30 am. With characteristic wit, she tells you how there was “no time for post-partum depression” and she was back to work in exactly ten days, losing the twenty-eight kilograms put on during her pregnancy pretty quickly.

You cannot but appreciate the resilience of this woman as she goes on to explain how on the business front there was a time when Mydala had its due diligence done and as much as closed in on a term sheet with an investor. Only that, on the day of the formal document-signing, the investor backed out. While it was a devastating blow to the business, it did teach her some very important lessons, the primary being the “need to innovate”.

While the company went on to be funded by Info Edge later, the lessons learnt stand the test of time. Irrespective of the cash in the bank, she confesses to run an extremely cash-conscious operation, so much so that “it takes some thinking to buy something as small as plants for the office”.

Did she have a brush with the patriarchal face of the start-up world?

Anisha tells me how during the initial fundraising stage, she was discounted by many an investor, one even calling her “too pregnant”. While she laughs it off now with a shrug, the irony is only too apparent. She recalls how the investor chose to speak to her male co-founder referring to her only in the third person, confident that after childbirth, “she wouldn’t come back”. A conversation that Anisha chose to end by telling the investor in no unequivocal terms: “It is my company and the end call will be mine.” She is quick to point out though that for every such person, she has also met some really “cool people” who have turned out to be her mentors.

More than the glass ceiling, Anisha feels it is the ability to second-guess their own capabilities that are stopping women in achieving their true potential. That, and the fact that as a gender, women aren’t too supportive of each other. She points out how women make “great friends, super sisters, mothers and daughters” but somehow, “we don’t stand up as much for fellow women professionals”. That explains why after informally mentoring women, Anisha is now toying with the idea of doing it formally. As she says, “People who have a voice need to give back to society.”

As the conversation veers to her own work-life balance, Anisha points out that it indeed is a tough call for spouses sharing a workspace. When asked if she would recommend spouses to come together to co-found a company, she quips, “This needs not just second-guessing but perhaps guessing forty times.”

She cautions that it takes a toll as office talk finds its way home.

Besides, “It takes a seriously secure guy to report to his wife. But they do it secretly at home anyway!” As for the working-mom guilt, Anisha confesses her brush with it is as frequent as brushing her teeth. Spending quality time with her kids is therefore unnegotiable. “Between 7 pm and 9 pm [the time earmarked for her daughters], you need to be god to get my attention,” she says determinedly. Such single-minded devotion was sure to be rewarded and Anisha’s reward came when, at her daughter’s latest parent-teacher meeting, she was told how her daughter seems to have been brought up with so much genuine love and effort that it shows in her demeanour. Anisha recalls bawling unabashedly in front of the teacher and other parents.

When queried about her future plans, she promises to “ring the NASDAQ bell someday”. It is a business goal all right, she tells me, but more than that, she wants her daughter to grow up with enough role models. “It is only when our daughters hear of more women entrepreneurs will they think it’s the norm rather than the exception,” she says. Sure enough, her daughter wants to grow up to run her own company!

“With all its ups and downs and your own initial fears, has the entrepreneurial journey been worth it and would you recommend it to others?” I ask. Anisha’s answer puts a stop to any further conjecture. “I have woken up each day with gratitude, charged and excited. How many people get to do it?”

Excerpted with permission from Dare to Be: 14 Fearless Women Who Gave Wings To Their Dreams, Rinku Paul and Puja Singhal, Penguin Books.