Harsh Jain and the art of starting over

Harsh Jain had a cricket problem before he had a cricket company. He had been playing fantasy football since 2001, following real players through an imaginary team of his own. When the Indian Premier League arrived in 2008, he went looking for the cricket equivalent. Here was a tournament designed to turn evenings into appointments. Surely somebody had supplied the accompanying argument about whose team was better.

The options disappointed him. So he and Bhavit Sheth began building Dream11 in Mumbai. The proposition had a fan’s appealing lack of modesty: the spectacle on television could be improved if the person on the sofa had something to do. Eighteen years later, Jain is still working on that proposition. Almost everything around it has changed, including the business that once paid for it.

The friend who said yes

Jain grew up in Mumbai and met Sheth at Greenlawns High School. School in Britain introduced him to fantasy football; engineering studies at the University of Pennsylvania took him farther from home. Picking players offered a way to keep a conversation going across countries. A league table could supply what a long-distance friendship occasionally lacks: a fresh reason to be insufferable on Monday.

He graduated in 2007, spent a brief internship at Microsoft and returned to the family business. His father, Anand Jain, was involved in manufacturing and real estate. The work included a special economic zone project whose timescale ran to decades. For a young engineer interested in sport, games and technology, the wait was considerable. The IPL offered an altogether faster clock.

Family backing helped finance the venture. That matters to this story: Jain had a cushion and has acknowledged it. He also had to learn the difference between access to money and knowing what to do with it. The first version of Dream11 accumulated features. A fan could find plenty to look at. The founders still needed a reason for enough fans to return and a reliable way to earn revenue.

The business that bought them time

The answer, for a while, was another business. Jain and Sheth built the social media agency Red Digital, earning money from client work while a smaller team kept the sports product alive. It was a practical arrangement with an unromantic advantage: customers paid for services. The founders could learn to sell while continuing to investigate whether their original idea had a future.

Red Digital worked with brands including Mumbai Indians, Dell and PepsiCo. Gozoop acquired it in 2013, consolidating the agency’s clients and employees into its operations. The detour gave the founders experience that a product specification could not. A client has deadlines, expectations and an irritating habit of asking what the work is worth. Such questions can be useful company for an ambitious idea.

Dream11 also became easier to fit into a person’s day. The founders moved toward a freemium, match-by-match format rather than expecting users to maintain a fantasy commitment over an entire season. Someone could pick a team before the next match and follow what happened. The unit of participation became smaller. The emotional investment could still be quite unreasonable, as anyone who follows sport would recognize.

Jain was learning the financial side too. From 2012 to 2014, he studied for an MBA at Columbia Business School. He wanted to understand financial statements, fundraising and the use of capital. The engineer who could imagine a product needed the vocabulary to defend a business. Going back to school while the venture remained uncertain made education part of the work rather than an ornament added afterward.

The fundraising took persistence. Jain and Sheth have described approaching roughly 150 investors without securing the backing they wanted. Their accounts emphasize what the refusals taught them about the numbers and the pitch. Vani Kola of Kalaari Capital became an important supporter. A good founder story can make the eventual cheque seem inevitable. The people repeatedly saying no had apparently missed that part of the script.

A very public arrival

By 2019, Dream11 had reached unicorn status. In 2020, it became the IPL’s title sponsor. For a business born alongside the tournament, this was a remarkably visible change of position. The name that once needed explaining now accompanied the competition itself. Few pitch decks can arrange for their central claim to be repeated during a cricket broadcast.

In November 2021, Dream Sports announced an $840 million investment at an $8 billion valuation. The investors included Falcon Edge, DST Global, D1 Capital, RedBird Capital and Tiger Global. That figure belongs to that funding event. It is a useful marker of how far the company had travelled, rather than a running score for everything that happened afterward.

The group’s ambition was already broader than fantasy contests. FanCode served sports viewers; DreamSetGo arranged sports experiences and travel. The Dream Sports Foundation supported young athletes. Jain’s interest in a fan’s day could stretch from a phone screen to a seat in a stadium, while the foundation addressed people hoping to compete on the other side of the boundary.

His own preferences remained agreeably specific. He supports Manchester United, Mumbai Indians and India’s cricket team. He remembers his first visit to Old Trafford particularly fondly: United beat Arsenal 2-1. When asked about future sporting trips in 2025, he named the Los Angeles Olympics in 2028. An executive can discuss an addressable market; a fan remembers the score.

The job behind the joke

Jain calls himself the Culture Enforcement Officer, an expansion of CEO with more personality than most corporate stationery permits. In his telling, hiring exceptional skills without shared values can produce damage, while people who fit the culture can develop their abilities. The title puts a human task at the centre of a company that depends heavily on technology.

“You can’t demand something from people that you’re not willing to do.”

Harsh Jain, 2024

Delegation is another part of his public advice. He has argued that founders need to hire people better than themselves and make room for them to work. There is a particular difficulty here for anyone whose company began as a personal frustration. Understanding the original customer does not qualify a founder to perform every job the growing business creates.

The engineering grew substantial enough to become an offering of its own. In late 2025, Jain promoted Dream Horizon, sharing technology developed inside Dream11 with a wider community of builders. His announcement described systems handling millions of concurrent fans. Cricket produces unforgiving deadlines: the match starts whether or not a server would prefer another five minutes.

His connection to Columbia also continued. In 2024, he joined professor and Cricinfo co-founder Vishal Misra for a discussion about AI in sport and academia. Their conversation addressed practical uses and industry collaboration. The following May, Jain addressed Columbia Engineering’s graduating students. He returned to an audience preparing to build things with a career full of examples of things needing revision.

When the cash engine stopped

Then came a much larger revision. Dream11 halted paid contests in August 2025 following India’s new online gaming legislation. Jain said the affected business accounted for 95 percent of Dream Sports’ revenue and all its profits. Years of scale could not shelter the group from the sudden loss of the mechanism that made the money.

His immediate response was to build rather than challenge the ban. In August, he said the company intended to retain its people and use their abilities on new products. That was a commitment made at a moment of shock, and its date matters. It expressed how he wanted to respond; the months that followed would involve the much harder work of assigning teams, budgets and responsibilities.

By December, Dream Sports had reorganized into eight independently led businesses. The arrangement spread leadership across units working on content, experiences, games and technology. It also changed the work people had joined to do. In March 2026, the company said about 700 employees had been placed into the startups and roughly 15 percent had chosen to leave.

In April, Jain described a portfolio of startups financed with profits earned in earlier years. Individual businesses had 18 to 24 months of runway. That is a different kind of management problem from operating one dominant engine. Each team needs to find demand and make its economics work. A shared parent can provide capital and experience. It cannot supply every answer in advance.

Still looking for the next match

On August 27, 2026, Dream11 announced that it had completed its move to a global sports engagement platform, discontinuing all prizes. The proposed destination combined content, statistics, community, experiences and social contests, with personalization built around fans’ preferences. Vaibhav Kokal was now Dream11’s CEO. Jain continued as CEO of parent Dream Sports.

The distinction is useful. The founder’s assignment now extends across the group, while the product that made its name has a separate chief executive. Its audience provides an opening for the new proposition. Whether people develop fresh habits around it remains a commercial question, to be answered by what they choose to watch, discuss and return to.

Jain began with something he wanted to play. He has since learned to run an agency, raise capital, build teams and reconsider a business whose old model had stopped working. The football fan is still recognizable beneath the executive titles. He knows the peculiar attraction of having an opinion about a match. The next task is persuading enough people to bring theirs along.