Prateek Dayal used to be an angry man, a struggling entrepreneur, confused husband and fervent technologist. Till one day, he finally said “fuck you” to the system. He was sick of listening to the system and living by its rules.

In December 2016, he announced to the world that he was transitioning from a male identity to a female one. The gender assigned to him at birth had begun to feel like a trap to him. He was ready to get out of it.

Today, Dayal has come alive as Hana Mohan, chief executive and cofounder of SupportBee, an e-mail-based customer support software. A digital nomad who divides times between cities in different continents, Hana (she prefers to be referred to by her adopted first name) is at times confused about life, but happy.

Three months ago, Hana posted a picture of herself sitting on a chair, sporting a masculine look, complete with a stubble and a cap, and wrote: “Like other ones, I enjoyed donning this look for a while. It couldn’t have lasted.”

It was the beginning of a new journey. For the outside world, this was the birth of Hana Mohan.

A land of locked identities

I first met Hana at the sidelines of a startup conference in Bengaluru four years ago — when she was still Dayal, one of the few entrepreneurs who had decided to bootstrap their startup even though it wasn’t fashionable.

Sitting here in Bengaluru, a city that residents proudly call the mecca of technology in India, I ask myself: What would she have gone through as a transwoman in India’s male-dominated startup ecosystem? And a larger question: What would the experience of transitioning to a different gender be like if, till a certain point, you were just like thousands of other IT executives in India who grew up in a middle-class family, were surrounded by a patriarchal society, went to an engineering college, got yourself a job and became part of the rat race?

How does one break free of these pre-defined structures?

Dayal’s journey to becoming Hana probably had some of the answers, and I reached out to her. We connected on Facebook and I spoke to her on Skype.

“Being trans is very hard. Being a woman is very hard. Being a woman of colour is very hard. The hardest thing is to be a trans woman of colour,” Hana told me over the call from Poblado, an upscale expat neighbourhood in Medellin, Colombia, one of her regular ports of call in the digital nomad life.

Hana’s transition was made more difficult by the fact that till quite recently, she couldn’t exactly identify the source of the dissatisfaction she felt constantly as a man. “When you have gender dysphoria, but don’t know what it is, you feel restless and associate it with whatever you know (could be the cause),” she says. There was no one to ask or talk to about these feelings, because the conversations were mainly about building billion dollar companies or coaxing the proverbial ‘hockey stick growth’ out of your startup. As Dayal, she felt this constant anxiety, but used work incessantly to escape confusing thoughts. The hectic world of startups in Bengaluru was a great way to drown out the questions and insecurities.

She would struggle with bouts of depression, but chalked it up to the startup life, which swings between extremes of happy and sad days. “The last three-four years of my life, I just flooded my time with sports and work and physical exercise. I got obsessed and kept myself busy. Startups were like that. It was a good way to stay busy. And once I started, there was a pressure to be successful because I didn’t have any money,” says Hana.

“I know hundreds of people in India, but not one of them is gay, lesbian or trans,” says Hana. The only time she met a transgender person was at a party in Bengaluru. “But I didn’t have the courage to go talk to her,” she says. India’s startup ecosystem, much like the world Dayal and thousands of Indian engineers grow up in, is yet another bubble made up of mostly cis men — males who identify as male and are what society calls “normal”. There was simply no space, no context for a confused young Prateek Dayal to talk openly about the gender anxiety and depression he was going through.

“The toxicity of the entrepreneurship culture is that we don’t accept the fact that individuals who start these companies are all vulnerable. At the end of the day, when you are constantly trying to project the fact that you are a superhero, it starts adding to the stress,” says Zainab Bawa, cofounder of HasGeek. Dayal has been a popular speaker at a HasGeek conference.

“Entrepreneurs are known to put up a brave face while they might be going through terrible ups and downs. They go through different phases, they are either very excited and on super highs, or they are in deep doubt,” said Sunil Patro, founder of SignEasy. Patro, who met Dayal around 2011 in Bengaluru, says that friends and family who don’t judge you based on the success or failure of the company should be an entrepreneur’s first port of call in times of crisis.

The loss of privilege

Like many people who transition into another gender later in life, for Dayal too it was a difficult change. Even tougher was the realisation that he was going to have to fight for the things that he had taken for granted as a man. “I started accepting the possibility that I’ll have to transition to feel better and I was completely paralysed. That’s the first time I realised how much privilege I would lose simply by switching over to the other side and how that’s just a fact of life for women and trans people or minorities,” says Hana.

The feeling of vulnerability was new. “I had never felt (physically) vulnerable in my life. I never felt that there’s a possibility that somebody could attack me, hurt me, simply because of who I am, not because of anything I did,” says Hana.

“As a guy I took everything for granted,” she says, talking about discussions she read on Reddit communities focussed on women and trans people, where individuals talk about how hard it is to be taken seriously in a hyper-competitive professional space as a woman or transgendered individual.

This is true for most parts and a revealing Twitter thread that went viral recently illustrates this well. Martin Schneider, a writer and editor, did an e-mail experiment. He exchanged his email signature with that of a female co-worker, Nicole, and found that suddenly everyone including clients, prospects and his boss stopped taking him seriously. “I was in hell. Everything I asked or suggested was questioned. Clients I could do in my sleep were condescending. One asked if I was single,” Schneider tweeted.

“Even people in technology like us who think we are intellectually more advanced don’t comprehend the problem,” says Hana. Why are there so few female CEOs or founders compared to their male counterparts, she questions.

Hana’s beginnings

Born to Pradeep and Kamini Dayal, Prateek/Hana had a typical middle-class upbringing. He* grew up primarily in Uttar Pradesh where his father worked as an engineer in the Indian Railways and his mother, a PhD in economics, taught students in school.

Getting their only son a decent education was a big deal for them. After finishing school in 2000, Dayal went to IIT-Guwahati, one of the top engineering colleges in the country, in 2001.

He was attracted to women’s clothing from a young age. Around the age of 12, when he hit puberty, he tried on some feminine clothes at home. He found it strangely attractive. “I was very ashamed of this, honestly. We grow up with this notion of admiring the other gender to the point you want to become like them. This really trips a lot of people up. Trans people think this is a normal human emotion. But for other people… it never crosses their mind to want to become the other gender,” says Hana.

The reason most trans people start with cross-dressing is because that’s the only thing they associate strongly with a sense of gender. “That’s the only way your brain keeps signalling to you that something is wrong,” says Hana.

For the longest time, Dayal thought that he was just cross-dressing and brushed deeper questions about his gender aside. “I knew it was a Pandora’s box. I had a feeling that if I looked at it too hard, it would take over my life and I believed that would be a bad thing,” says Hana. For many years, Dayal wouldn’t talk about his feelings to anyone else.

“I grew up in my own little shell and once I was at IIT, it was another isolating environment in the sense that there are few women in IIT, there are no real discussions on sexuality, gender. It was like an extension of the bubble I grew up in,” Hana points out.

Dayal graduated from IIT in 2005, in the bottom 25% of his class. But he was also one of the only people in college at the time who managed to get four of his papers published in the IEEE journal (this is a feat by student standards). After graduating, he had short stints at companies such as Tejas Networks and Bandspeed in Bengaluru. He couldn’t stick to a job for long. “I was termed what is called a ‘high maintenance employee’. In the sense that it takes a lot to keep me excited. It wasn’t their fault,” says Hana.

This is when Dayal started projects that would eventually make way for him to become an entrepreneur. It was a way of keeping busy and warding off confusing thoughts about his sexuality. At a company he worked in, Dayal met Nithya Rajaram, and they struck up a close friendship. He confided his deepest fears and insecurities to her. A few years later, they got married (they are separated now).

Dayal’s first company was called Bangalore Bytes. It was a side project to bring offline deals online that didn’t take off. Later, with Nithya he started Muziboo, a karaoke site. At its peak in 2010, it reached a million people and he was signing up nearly 30,000 people every month. He shut the business because it wasn’t making any money and record companies in India began sending him takedown notices citing copyright violation. It wasn’t worth the trouble.

His next startup, also founded with Nithya, was SupportBee, an e-mail ticketing system. Today, the subscription-based business brings in nearly $300,000 a year to the team, according to a blogpost written by Dayal in May 2016. He was living in Medellin by then. “Five of us can live a good life. Work on interesting problems. And not be shackled to a desk job,” Hana tells me over Skype.

Nearly half a million dollars a year is meaningful income for most companies and entrepreneurs, but the world of startups can be brutal, and is fertile ground for the Icarus complex. “The irony that I find in the startup ecosystem in India and the reason why I’m happy to not be there is that I can’t take the way people spit on businesses that make, let’s say, $50,000 a month while they can barely make their own rent, eat high quality food or travel,” says Hana.

Alongside building his company, Dayal continued to delve deeper into himself in an attempt to dissect his depression and find what was making him unhappy.

Clearing out the clutter

Avinasha Shastry, who works as chief technology officer at SupportBee, and Dayal would hang out after work and talk about life in general. The two first met when Shastry, a young engineer at another startup, went to Dayal to clear some doubts. “I decided that I needed to work with someone who can teach me things. He’s been a big influence in my life,” says Shastry, who is off to Bali this month.

Shastry tells me that Hana’s journey truly began when she started delving deeper into the concepts of mindspace, mindfulness, and meditation. “Prateek explained the concept of mindspace to me. You have finite mindspace in the head, which is dominated by various issues. He was trying to figure out how to clear the clutter out and focus,” says Shastry.

Hana’s journey also involves a supportive partner — and, shocking as it may be to some, LSD. Nithya and Dayal were in their early 20s when they decided to get married. They were in the same company, Bandspeed, which later shut down its Bangalore centre. After starting SupportBee, the team went to Startup Chile, a government-funded accelerator program. That’s when the team became truly nomadic.

“She was a very supportive partner. She wasn’t judgemental about my gender confusion,” says Hana. “The only times we would have a good time is when I was cross-dressing, when I thought I was escaping my real life,” she says.

Nithya reckons that it was around six-seven months ago that Dayal told her about his decision to transition. He told her, “I found the vocabulary for the struggle I’m going through. Gender dysphoria.”

“When we were together, we thought the mood swings and depression were part of the startup journey. After all, it is not the usual salaried person’s life,” says Nithya, who now lives in San Diego. “We both were unaware and almost illiterate about this subject. It was like fighting in the dark,” recalls Nithya, who is 35 years old. “There was no understanding of these issues. Forget the startup world, even the world at large doesn’t have any acceptance and awareness,” says Nithya. The two separated in 2012, way before Dayal seriously started thinking of transitioning, but continued building SupportBee.

“We could have never done this if Hana was in India. If you look at Meetup.com, you’ll find a few groups and your peers in the US… Hana can go to Bangalore and start a group, but I don’t know if anyone will join the group,” says Nithya.

In Bengaluru, there is support for queer identities, but not enough. “There’s this tendency among people in Bengaluru to think of it as a cool city. So, there are ways in which people behave cool masculinely and cool femininely. That reinforces certain gender stereotypes and that is a problem for people who may be questioning their gender,” writer and marketing professional Nadika Nadja explains.

Among the top eight cities in India, Bengaluru and Chennai probably have the most robust support networks for trans people, she adds. Yet, Bengaluru’s thriving queer scene doesn’t often help people like Dayal, who are from a “different world” (not from traditionally more liberal and open-minded spaces such as art, theatre, writing).

In the absence of much support from outside, most of Dayal’s education about gender dysphoria happened on Reddit (asktransgender). “I thought Reddit was a timesink (and it is). But if you are part of a community, you get a lot of support,” says Hana. On Reddit, Dayal found resources, blogs and like-minded people.

Acid or lysergic acid diethylamide (LSD) also played a crucial role in Dayal’s acceptance of Hana. It must be something when a person like Steve Jobs says that “dropping acid” was the most profound experience in his life. Trippers often use acid or LSD to ask themselves hard questions such as “what is the meaning of life.” Some experience what is called “ego death” while on a trip and come out with a lot more clarity. Ego death, a condition referred to by many acid users, refers to the mental state in which your consciousness is reborn. Many who go through this experience call it therapeutic.

Dayal had been using psychedelic drugs since 2014 to fight depression. Last year, in July, it got to a point that he was very anxious and during a party in Vietnam, it became obvious to him that he had to come out. “The first (acid) trip helped me understand how depression has been affecting my life and motivated me to find a way out,” Hana says.

In many ways, it was perfect timing. He had a stable income and a visa to live in Medellin. The seeds of wanting to explore his gender further were planed in his head in 2014, on his first trip to San Francisco. “That’s the first time I met people who lived their lives and didn’t give a shit about what the world thought,” says Hana, who started growing her hair around that time.

On a vacation to Ecuador in August last year, where she taught herself Spanish, she bought a new wardrobe. “In a new environment you can be whoever you want. I used that as an opportunity to explore myself,” says Hana.

For those who want to come out, a change of scene often helps. Nadja, for instance, has known that she is queer for many years but only came out in 2013 after moving from Chennai to Bengaluru. “My biggest problem was how and where… In Chennai, too many people knew me from my earlier life,” says Nadja, 35. “My mental health took a big beating and I decided that the only way to get out of that loop was to come out,” said Nadja.

For Hana, it was a similar experience. Initially, she thought it was only about cross-dressing and some sort of “sexual fetish”, but then she realised that she was “much calmer, happier and lighter” after embracing her female identity.

At the end of the trip to Ecuador, Hana talked to her parents. “They went quiet for a few days, did their own reading and research and then they came back very supportive. It was hard for them, but they’ve been supportive,” says Hana. Dayal then told his friends and the team at SupportBee in September.

I tried reaching out to her parents for this story but wasn’t very successful and to respect their privacy I didn’t pursue them hard enough.

Avinasha Shastry is still a core team member at SupportBee. He, too, has chosen to pursue a nomadic lifestyle and is off to Bali next month. Nithya married again and is mother to a two-month-old daughter.

As for Hana, the plan is to run SupportBee, learn more about herself, and perhaps help out people who are supporting causes that concern the queer community.

“The most inspiring people are the ones who are trans despite it being very hard for them. The ones who don’t have a lot of money… the unnamed people,” says Hana, who has been writing regularly about her experiences as a transwoman on her Medium blog.

We wish her luck on this journey.

*We have referred to Prateek Dayal pre-gender transition using the male pronouns ‘he/him/his’.

Hear the story of another transgender person from Bengaluru:

The Outliers 4: From Pune’s streets to Bengaluru’s IT corridor, a transwoman tells us how

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