The birth of India’s online real money gaming industry can be traced to a cramped London apartment in 2005, where a group of Indian students gathered around a table playing cards after classes. “This industry we see thriving in India today was born in my room in London where I was studying,” says Deepak Gullapalli, founder and CEO of Head Digital Works, the company behind online rummy platform A23, initially launched as Ace2Three in 2006. It became the first Indian company to introduce online rummy and real-money gaming later in 2009.

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While his friends dealt physical cards for their nightly rummy games, Gullapalli noticed one roommate playing Solitaire on Microsoft Windows — the iconic card game that had shipped with Windows since 1990, becoming perhaps the most played computer game in history. In that pre-smartphone era of 2005, when Nokia’s monochrome Snake was the height of mobile gaming and the iPhone was still two years away, Solitaire was a ubiquitous digital diversion, instantly recognisable with its green background and bouncing cards that celebrated a win.

The question that sparked a multi-billion-dollar industry was disarmingly simple: “Why are you not playing rummy on the computer?”

For Gullapalli, rummy wasn’t just any card game. Coming from Andhra Pradesh, where the game is deeply embedded in its cultural fabric, his earliest memory of playing rummy was on a train journey with his family at age 10. “My mother was a very good rummy player. In fact, she was the one who actually tested our software initially,” he recalls with pride. In the Telugu-speaking regions, rummy transcends mere entertainment—it’s always been a social ritual played during festivals like Diwali and Sankranti, a multigenerational activity that bridges age gaps and reinforces community bonds, Gullapalli recalls.

When Gullapalli returned to India in 2006 with his master’s degree in Business Systems from Middlesex University, his initial business model seems quaint by today’s standards – he planned to sell rummy games on CD-ROMs. Like a beginner dealt an unpromising hand, he started with modest ambitions. “I never thought I would be building a business out of it,” Gullapalli admits. He thought he would make a quick buck by selling the CDs or selling the software and just do it as a hobby.

But destiny had other things in store. The garage startup story that followed has all the hallmarks of entrepreneurial perseverance – a high-stakes game where Gullapalli was playing with limited chips. Initial capital came from unlikely sources – `5 lakh from his mother’s savings, another `5 lakh from his London earnings. The company’s first office was a 150-square-foot room located under a water tank in his apartment building, a far cry from the `1,378 crore it would generate in revenue while posting a profit of around `85 crore in FY24. “I couldn’t even buy computers. I had to rent computers on a monthly rent of `2,500,” Gullapalli remembers.

With just two rented computers, Gullapalli assembled a small team including Shiva P (now VP of technology business platform) and Ranadeep Tujala (enterprise architect).

The evolution from CD-ROM concept to online platform came with the realisation that rummy’s multiplayer nature made it unsuitable for solo play against computer algorithms. “This is a game that is played with multiplayers. The CD-ROM format where you play against the computer didn’t really work because the computer had to think,” he explains. Internet gaming was just beginning, offering the perfect opportunity to develop a platform where people could play against each other remotely.

A pivotal moment came when Gullapalli joined Party Gaming (now Entain) as a product manager in 2007-2008. “I spent about a year and a half and really got to know the mechanics of online poker, online gaming,” he says. While maintaining his day job from 9 to 6, Gullapalli would work on his startup from 6:30 to 9:30 pm.

When he eventually left Party Gaming to focus full-time on his venture, Gullapalli employed his best ‘bluff’. “I didn’t tell my mother that I quit my job, I told her I lost my job due to layoffs to avoid concern.”

The company launched its real money gaming in June 2009 after securing legal opinion. “I still remember day one when our revenue was about `8,000,” Gullapalli says. Within a year, the business became cash-positive, allowing reinvestment in growth.

The industry’s legitimacy received a significant boost in 2010 when Matrix Partners came on board, becoming the first venture capital firm to invest in an Indian gaming company. The investment brought structure and governance to what had been a bootstrapped operation. “They called me and in three weeks the money was in the bank,” Gullapalli says.

Gullapalli’s comfort with business risk may stem from his family background. His father and grandfather were in the film distribution business, an industry he describes as “a much bigger gamble” than online gaming. This early exposure to high-stakes decision-making left a lasting mark on his entrepreneurial approach.

Legal challenges have been constant companions on the journey. “Trying to convince people that we are a legitimate Indian startup technology company been the most difficult part of the work,” Gullapalli added. Despite landmark judgements by the Supreme Court dating as far back as 1957 recognising rummy as a game of skill — where success depends on knowledge and strategy versus game of chance which is purely based on luck — many states have brought in state-level amendments to restrict all real-money gaming.

The company faced perhaps its most significant crisis when Telangana banned online rummy in 2017, forcing the entire team to temporarily relocate to Bengaluru. Despite challenges, the company has continued to be at the forefront of

legal challenges to these restrictions, arguing that rummy’s classification as a game of skill should protect it under Article 19(1)(g) of the Indian Constitution.

Gullapalli’s best hand was dealt through the smartphone revolution around 2013-2014, which transformed access and expanded the market exponentially. Until 2014, it was a pure desktop game. Mobile technology opened gaming to millions of new users, particularly in the hinterlands where smartphone penetration outpaced PC adoption.

Since 2006, Gullapalli says, he has methodically grown his company to a platform with over 55 million users and over 600 employees, operating multiple verticals in real money gaming including Rummy, Fantasy Sports and other casual games under its brands A23 and Cricket.com. It also recently expanded into online poker with the acquisition of Adda52. That’s exactly like a player building a winning hand card by card.